TIN 1
dinitro compounds (eq 3).16 Under the same conditions, a gemi-
Tin1
nal dinitro compound is reported to give the corresponding oxime
(eq 4).16 N-Nitrosamines are reduced by tin and HCl to the deni-
Sn
trosated amines (eq 5),17 whereas the corresponding Zinc reduc-
tion produces the hydrazines.
[7440-31-5] Sn (MW 118.71)
CO2H CO2H
InChI = 1/Sn
O2N NO2 Sn H2N NH2
InChIKey = ATJFFYVFTNAWJD-UHFFFAOYAJ
(1)
HCl
(with HCl, reduces a variety of functional groups;2 stereoselec-
NO2 NH2
tive allylation of carbonyl compounds;3 in situ generation of tin
enolates for directed aldol reactions4)
H
NHCH2CO2H
N
Sn, HCl
ć% ć%
Physical Data: mp 232 C; bp <"2270 C; d 7.31 g cm-3.
(2)
Solubility: insol water, organic solvents; reacts with mineral 85%
MeO NO2
MeO N O
acids.
H
Form Supplied in: foil, moss, powder, granules, shot, and wire.
Preparative Methods: activated form is prepared from Tin(II) R1 R2 R1 R2
Sn, HCl
NO2 NH2 (3)
Chloride in THF by reduction with Lithium Aluminum
O2N H2N
Hydride5 or Potassium metal;6 tin amalgam is prepared from
R1 R2 42 82% R1 R2
Mercury(II) Chloride and 30-mesh Sn in water;7 tin copper
R1, R2 = Me, Et
couple is prepared from Copper(II) Acetate and 30-mesh tin in
Sn, HCl
acetic acid.8
(4)
Handling, Storage, and Precautions: incompatible with strong
O2N NO2 85%
NOH
acids and strong oxidizing agents; powdered form is air and
Ph
Ph
moisture sensitive and should not be inhaled or contacted with
Sn, HCl
(5)
N NO N H
the eyes or skin; amalgam is stored under water; tin copper
Me Me
couple is stored under ether.
Examples of reductions of other functional groups by tin and
HCl include the reduction of isoquinoline methiodides,18 of tetra-
hydrocarbazole to hexahydrocarbazole,19 and of 5-(chloromethyl)
uracil to thymine (eq 6),20 the selective debromination of 1,6-
Original Commentary
dibromo-2-naphthol (eq 7),21 and the reduction of anisoin to
Peter J. Steel deoxyanisoin,22 of anthraquinone to anthrone (eq 8),23 and of
University of Canterbury, Christchurch, New Zealand benzaldehydes to stilbenes.24
O O
Functional Group Reductions. The use of tin and Hy-
CH2Cl
Sn, HCl
drochloric Acid is a classical method for the reduction of a HN HN
(6)
variety of functional groups.2 However this procedure has de-
82%
O N O N
creased in importance since the development of catalytic hydro-
H H
genation and of metal hydride reducing agents, and the harsh
Br
reaction conditions (strong acids and high temperatures) are of-
OH OH
ten incompatible with other functional groups. Many reductions Sn, HBr
(7)
effected by tin are more conveniently carried out with Tin(II)
70%
Br Br
Chloride, which is soluble in some organic solvents. Never-
theless, the method is still used, most notably for the reduc-
O
O
tion of aromatic nitro compounds to amines, for which metal
Sn, HCl
hydrides are less effective (see Lithium Aluminum Hydride).
(8)
83%
Representative examples of standard procedures which utilize
Sn/HCl include the reductions of 2,6-dibromo-4-nitrophenol to
O
the aminophenol,9 2,4,6-trinitrobenzoic acid to the triamine (eq
1),10 and nitrobarbituric acid to the amine (uramil).11 Aromatic ni- Tin amalgam and hydrochloric acid is useful for the selective
tro group reductions with tin and hydrochloric acid have been em- reduction of the double bond of conjugated enediones in high
yield (eq 9)7 and for the controlled reduction of benzils to either
ployed in the preparation of functionalized paracyclophanes12 and
hemispherands.13 8-Nitroquinolines have been reduced to the cor- benzoins or deoxybenzoins.25 Tin amalgam in Acetic Acid also
responding amines with a combination of tin and tin(II) chloride.14 reduces benzoquinones to hydroquinones.7,26
In some cases the generated amines undergo further reactions
O
O
(eq 2).15 Sn/Hg, HCl
Ph
Ph
(9)
Ph
Ph
Sterically hindered aliphatic vicinal diamines have recently
90%
O
O
been prepared by Sn/HCl reductions of the corresponding 1,2-
Avoid Skin Contact with All Reagents
2 TIN
Tin reductions have also been used for the conversion of aryl-
Sn, Al, THF, H2O
Ph
Br Ph
+ (13)
sulfonyl chlorides to the corresponding thiols27 and for the prepa-
PhCHO
ration of Thiophosgene from thiocarbonyl perchloride.28 Metal- OH OH
87%
3:2
lic tin has recently been used for the in situ generation of low-
valent bismuth and titanium species that catalyze cyclizations to
Ph
3-hydroxycephems (eq 10).29 A tin copper couple has been used
Sn, Al, THF, H2O
Ph
for the selective debromination of activated dibromides (eq 11),8 Ph Cl
(14)
PhCHO
in cases where the more commonly employed Zinc/Copper
OH
100%
Couple leads to overreduction.
Ph
RCONH S-SO2Ph
RCONH Sn, Al, THF, H2O
S
R
Cl Sn, BiCl4 Ph Cl
(10)
N
RCH=CHCHO
N
O py, DMF OH
100%
OR
OR
O
42 82%
RO2C
(15)
CO2R
Ph Ph
Sn, Al, THF, H2O
Br
Br
Sn/Cu, THF +
Br Br
Ph Ph
(11)
Ph(Me)CHCHO
HO2C CO2H OH OH
81%
85%
HO2C CO2H
3:1
Ph
CO2Et
Barbier-type Allylations and Related Reactions. The reac-
Sn, Al, DME
Br
tion of carbonyl compounds with allylmetal reagents to give ho-
(16)
O
PhCHO
moallylic alcohols is an extremely important reaction in organic
75%
O
synthesis.3,30 Metallic tin can be used for the in situ generation
of diallyltin dihalides for subsequent reaction with aldehydes or
ketones in good yield (eq 12).31 The procedure is considerably
The Sn/Al procedure has been further extended to the reac-
more convenient than that involving isolation of allyltin interme-
tions of propargylic halides and such reactions can give both
diates and can be carried out in the presence of water.32 Moderate
alkynic and allenic products, depending on the reaction conditions
asymmetric induction is observed when the reaction is carried
(eq 17).43 The direct reaction of metallic tin with simple alkyl
out in the presence of monosodium (+)-diethyl tartrate.33 The
halides to give dialkyltin dihalides is an industrially important
yields are improved by sonication34 and this procedure has re- reaction and is usually restricted to the reactions of alkyl iodides.44
cently been applied to chain extensions of carbohydrates.35 The
More recently, a phase-transfer catalyzed procedure has been
reaction can be made catalytic by electrochemical regeneration of
developed that facilitates reactions of alkyl bromides and chlo-
the tin reagent.36
rides.45
Sn, THF
Ph
TMS
Br
+ PhCHO (12)
Sn, Al
Ph
82% Ph
+ (17)
OH TMS CH2I
"
PhCHO
OH TMS
OH
70%
A further improvement involves performing the reaction in
Solvent: MeCN 1:5
the presence of Aluminum powder in a THF water mixture.32
Diglyme 8:1
Under these conditions, allyl chloride also reacts37 and yields
are improved for reactions of substituted allyl halides. In such
cases the diastereoselectivity is dependent on the specific reac-
tants and reaction conditions. For example the Sn/Al reaction of Tin Enolates. Tin enolates are useful intermediates for
benzaldehyde with crotyl bromide gives the syn diastereoisomer as use in directed aldol reactions.4,46 Tin(II) enolates are usually
the major product (eq 13),32 whereas reaction with cinnamyl chlo- prepared47 by reaction of enolizable ketones with Tin(II) Triflu-
ride occurs with exclusive anti selectivity (eq 14).38 Under the oromethanesulfonate, but can also be prepared from reactions
same conditions cinnamyl chloride reacts with enals by exclusive of Ä…-bromocarbonyl compounds with activated metallic tin. Such
1,2-regioselective addition and complete anti diastereoselecti- enolates react with aldehydes and ketones under mild conditions
vity and with 2-phenylpropanal with moderate Cram selectivity to give aldols, generally in high yield (eq 18).48 With Ä…-substituted
(eq 15).38 These reactions are compatible with a variety of enolates high syn selectivity is observed (eq 19);48 this is the oppo-
other functional groups,32,39,40 although in some cases these may site selectivity to that found with tin(IV) enolates. It has recently
induce further reactions (eq 16).40 A mechanistic study of the been shown that such reactions can be carried out in aqueous me-
tin-promoted reactions of allylic iodides with benzaldehydes has dia with unactivated tin powder, but that under these conditions the
recently been reported.41 It has also recently been shown that metal enolate is probably not involved; a single-electron-transfer
allylic alcohols undergo similar reactions with metallic tin in the mechanism has been suggested.49 In a related reaction, metallic
presence of Chlorotrimethylsilane and Sodium Iodide.42 Under tin has been used to generate a highly functionalized tin(II) enolate
these conditions, substituted allylic alcohols undergo carbon for alkylation of an azetidinone as part of a carbapenam synthesis
carbon bond formation to the less substituted allylic carbon.42 (eq 20).50
A list of General Abbreviations appears on the front Endpapers
TIN 3
R2 R3 on an electrodeficient aromatic ring were reduced simultaneously
R2 R3
Sn, R1COR2
R1 R1
under these reaction conditions (eq 26).56
R1 (18)
R2
Br
28 99%
O OH
O
NO2
Sn, HCl
1. Sn, DMF
Br Br
Ph
Ph Ph Ph Ph EtOH, reflux
+
Br
2. PhCHO,  78 °C 65%
(19)
O2N
O
OH O OH O
93%
93:7
NH2
Br Br (23)
OTBDMS
N2
OAc Sn, DMF
H2N
+ O
Br
75%
NH
O O
O
OMe OMe
H
N2
OR
O NO2 N O
Sn, HCl aq
(24)
(20)
MeOH
O CN
O
Br Br
77%
NH
O
CN
CO2Et
²:Ä… = 3:1
Tin(II) ester enolates can also be prepared by reaction of
+
- +
Cl H3N
Ä…-bromo carboxylic acid esters for Reformatsky-type reactions O2N NO2 NH3 Cl-
under very mild conditions (eq 21).5 Reaction of an Ä…-diketone
Sn, HCl
(25)
or Ä…-keto aldehyde with activated metallic tin produces a tin(II)
Br Br 61%
S S
enediolate that reacts with aldehydes to produce Ä…,²-dihydroxy
ketones in high yield (eq 22).51 The diastereoselectivity of this
reaction can is controlled by the addition of hexafluorobenzene.
NO2 NH2
F F F F
OH
Sn, HCl
Sn, THF
(26)
Br CO2Et
PhCHO + (21)
CO2Et
EtOH
Ph
83%
F F F F
85%
N3 NH2
Sn OH
O O
Sn, THF RCHO
O O
R
(22)
73 95% Reductions of aliphatic nitriles to the corresponding amines
OH O
have been described with concomitant hydrolysis of an oxazolidi-
none function to the corresponding acid in a one-step procedure
(eq 27).57 Sterically hindered quaternary nitro groups could also
be selectively and cleanly reduced to the corresponding amine (eq
28). This method was reported to be more efficient and selective
compared to the traditional catalytic hydrogenation methods.54
First Update
Jean-François Poisson
O
Université Joseph Fourier (Grenoble I), Grenoble, France
N
Sn, HCl
Functional Group Reductions. The reduction of the nitro
CN
70%
function by tin metal in acidic media is a very useful tool in
organic synthesis. This method is now mostly used for the re-
duction of aromatic nitro compounds and there are many exam- Cl OH
ples. The reduction of the nitro group is efficiently achieved in
O
the presence of aromatic bromides (eq 23),52 nitriles (eq 24),53
(27)
or isolated double bonds.54 In some cases, aromatic bromides are
NH2·HCl
also reduced. For example, 2,5-dibromo-3,4-dinitrothiophene is
Cl
reduced to 3,4-diaminothiophene (eq 25).55 A nitro and an azide
Avoid Skin Contact with All Reagents
4 TIN
alized in water. The addition of allyltin to aldehydes is feasible
O
without solvent using ultrasound to activate the metal, leading
NO2
to the homoallylic alcohol in very high yield (eq 35).67 Under
1. Sn, AcOH
H3CO
these conditions, ketones failed to react. In anhydrous methanol,
2. AcCl, py
CH2Cl2 the addition of allyltin is promoted by trimethylsilyl chloride (eq
H3C
64%
36).68 Ketones also react, leading to the quaternary homoallylic
N
alcohol in low yields. The yields can be improved by addition of
CH3
tetrabutylammonium bromide.
O
NHAc
H3CO
(28)
NO2
Sn
H3C
MeO OMe
HCl (36%)
N
60%
CH3
MeO
NO2 NO2 OMe
Indoles are selectively reduced to the corresponding indolines
in high yield (eq 29). The product thus obtained does not need
purification in most cases.58 The reduction of indoquinoline in the
NH2 (31)
presence of acetic anhydride afforded the corresponding indolyl
MeO OMe
acetate (eq 30).59
Sn, HCl
MeO N OMe
Cl
EtOH
N
O
97%
H
NO2 HN H
H
H
Sn, HCO2H
H
(32)
(29)
Cl toluene, reflux
H H
Dean-Stark
N
75%
H
O O
O OAc
NO2 NHBoc
Sn
Sn/NH4Cl
(30)
(33)
AcOH/Ac2O R R
N N Boc2O
(1/1)
H H
MeOH, ultrasound
90%
80 90%
N N
R = Akyl, X, OH, NH2, CHO
Under the acidic alcoholic conditions of reduction, the nitro-
gen can react further with esters to form lactams in situ.60 From
SO2Na SH
Sn, HCl
properly substituted dinitroaromatic compounds, acridines are
R R (34)
78 96%
synthesized in good yields (eq 31).61 Convenient procedures for
the formation of N-formamides from nitro aromatic compounds
have been developed: the reaction is performed using formic acid
R = 4-Me, 4-Cl, 4-OMe, 4-F, 3-CF3
instead of hydrochloric acid (eq 32).62 Similarly, carbamates can
OH
also be obtained when the reduction is performed with ammonium O
Sn, ultrasound
Br
(35)
chloride in the presence of BOC anhydride or ethyl chlorofor- +
no solvent R
R H
H
mate (eq 33).63 Finally, the sodium salt of arenesulfinic acids are
82 98%
conveniently reduced to the corresponding thiols in high yields
R = Ar, cinamyl
(eq 34).64
O
Barbier-type Allylations and Related Reactions. Metallic
Sn
tin is used to generate an allyltin species in situ from allyl bro- Br
+
Me3SiCl, MeOH
mide, which can react with carbonyl electrophiles. Tin metal can
be used directly with the commercially available allyl bromide.
OH
The tin can be preactivated by washing with sodium hydroxide65
or it can be generated by reduction of tin(II) chloride in liquid
(36)
ammonia.66 Activation can also be carried out within the reac-
tion media either by sonication or by treatment with a Lewis or
Brłnsted acid. Reactions are normally performed in a mixture 14%
45% with Bu4NBr
of organic solvent and alcohols, although they can also be re-
A list of General Abbreviations appears on the front Endpapers
TIN 5
OHC
A noteworthy allyltin reagent is 2-bromopropenyltin, gener-
Br
O
ated from 2,3-dibromopropene. This reagent reacts in situ with
BnO OMe
aldehyde69 and is of great utility in that it leads to a vinyl bromide
Sn, ultrasound
that can react in other classical organic reactions (eq 37). When the CH3CN, H2O
BnO OBn
83%
addition is performed on a chiral aldehyde, the level of diastereos-
electivity can be excellent. It has been used in many complex total
syntheses.70 This reaction can be directly performed on ketals that
are deprotected in situ under the protic acidic reaction conditions
HO HO
(eq 38).71
(40)
+
O O
BnO OMe BnO OMe
Br
O H
Br
9:1
BnO OBn BnO OBn
TBDPSO
Sn, HBr
OH
EtOH, H2O
H
Br
80%
O
O
Sn, TBAI
H
H Br
DMI, H2O
HO
90%
O
(37)
TBDPSO
OH
H
O O
single diastereomer
O O
(41)
+
Br
OH OH
75:25
Br
OH Br
O
O
(38)
Sn, HBr
DMI = 1,3-dimethyl-2-imidazolidinone
H Et2O, H2O
90%
N N
The addition of crotyl bromide to aldehydes in the presence of
O
tin metal can, in principle, lead to the branched Å‚-product and
the linear Ä…-product (eq 39). For a long time, the Å‚-product was Br
NHBoc
exclusively obtained, with variable diastereoselectivities. Re-
H
cently, it was shown that the branched product is the kinetic
NH4Cl aq sat/THF (4/1)
product.72 Indeed, with longer reaction times, the initially formed
56%
OH O
Å‚-adduct is slowly converted into the thermodynamically more
stable trans-Ä…-adduct, which is finally the only observed product.
BocHN BocHN
(42)
+
OH
Br
5:1
OH OH OH OH
Sn,H2O
O
Me
Imidazoles in the presence of alkyl chloroformates are allylated
4 h
by allyl bromide and tin metal in anhydrous THF with excellent
H
(39)
yields (eq 43).77 In this case tin was activated prior to use by
OH
washing with aq sodium hydroxide and water.65
same conditions
CO2Me
Br
H 1.
24 h
N
N
Sn, THF
H
(43)
2. ClCO2Me, NEt3
The reaction of allyltin with unprotected carbohydrates in N
N
74%
water73 or sugar-derived Ä…-alkoxy substituted aldehydes leads
CO2Me
to the syn-product with very good levels of selectivity (eq
40).74 The addition of crotyltin to Ä…-alkoxy substituted aldehydes Another interesting allylation protocol uses InCl3 and tin to
occurs with very good facial selectivity, this time in favor of generate the allylmetal species that reacts with carbonyl elec-
the anti-product, but with a modest syn/anti ratio between the trophiles with a good level of diastereoselectivity (eq 44).78 As
homoallylic alcohol and the allylic substituent (eq 41). In this the reaction is performed in water, unprotected sugars can also
precise example, allyltin gave the most selective reaction among be used, leading to the allylated product in good yield and high
all the tested transition metals and Lewis acids.75 The addition syn-selectivity (comparable to the selectivity obtained with tin
of the allyltin organometallic to an Ä…-aminosubstituted aldehyde metal alone) (eq 45). This procedure has been applied to
derived from an amino acid leads to the anti-product as the Ä…-trifluorohemiketals (eq 46),79 and also to difluorobromo allyl-
major isomer (eq 42).76 In most of the tested examples, the authors and propargyl bromide that react in good yield with various
obtained the opposite selectivity using allylzinc bromide. aldehydes (eq 47).80
Avoid Skin Contact with All Reagents
6 TIN
O OH
3. (a) Roush, W. R., Comprehensive Organic Synthesis 1991, 2, 1.
(b) Yamamoto, Y.; Asao, N., Chem. Rev. 1993, 93, 2207.
Br
EtO2C
H
4. Chan, T.-H., Comprehensive Organic Synthesis 1991, 2, 595.
(44)
Sn, InCl3, H2O
CO2Et
5. Harada, T.; Mukaiyama, T., Chem. Lett. 1982, 161.
65%
dr = 99:1
6. Kato, J.; Mukaiyama, T., Chem. Lett. 1983, 1727.
7. Schaefer, J. P., J. Org. Chem. 1960, 25, 2027.
8. Dowd, P.; Marwaha, L. K., J. Org. Chem. 1976, 41, 4035.
CHO
9. Hartman, W. W.; Dickey, J. B.; Stampfli, J. G., Org. Synth., Coll. Vol.
Br
1.
HO
OAc 1943, 2, 175.
Sn, InCl3, H2O
HO
AcO 10. Clarke, H. T.; Hartman, W. W., Org. Synth., Coll. Vol. 1932, 1, 444.
(45)
2. Ac2O, Py, DMAP
OH 11. Hartman, W. W.; Sheppard, O. E., Org. Synth., Coll. Vol. 1943, 2, 617.
AcO
85%
OH 12. Sheehan, M.; Cram, D. J., J. Am. Chem. Soc. 1969, 91, 3544.
OAc
13. Doxsee, K. M.; Feigel, M.; Stewart, K. D.; Canary, J. W.; Knobler, C.
OH
OAc
B.; Cram, D. J., J. Am. Chem. Soc. 1987, 109, 3098.
D-Mannose OAc
14. Carroll, F. I.; Berrang, B. D.; Linn, C. P., J. Med. Chem. 1979, 22, 1363.
dr = 94:6
15. (a) Wear, R. L.; Hamilton, C. S., J. Am. Chem. Soc. 1950, 72, 2893.
OEt OH (b) Petrow, V. A.; Stack, M. V.; Wragg, W. R., J. Chem. Soc. 1943, 316.
Sn, InCl3, H2O
(46) 16. Asaro, M. F.; Nakayama, I.; Wilson, R. B., Jr., J. Org. Chem. 1992, 57,
Br
F3C OH F3C
778.
85%
17. Fridman, A. L.; Mukhametshin, F. M.; Novikov, S. S., Russ. Chem. Rev.
(Engl. Transl.) 1971, 40, 34.
O
R2 Sn, InCl3
18. Wittig, G.; Streib, H., Justus Liebigs Ann. Chem. 1953, 584, 1.
+
R1 H H2O
19. Gurney, J.; Perkin, W. H., Jr.; Plant, S. G. P., J. Chem. Soc. 1927, 130,
CF2Br
46 67%
2676.
20. Skinner, W. A.; Schelstraete, M. G. M.; Baker, B. R., J. Org. Chem. 1960,
OH R2
25, 149.
(47)
21. Koelsch, C. F., Org. Synth., Coll. Vol. 1955, 3, 132.
R1
22. Carter, P. H.; Craig, J. C.; Lack, R. E.; Moyle, M., Org. Synth., Coll. Vol.
F
F
1973, 5, 339.
23. Meyer, K. H., Org. Synth., Coll. Vol. 1932, 1, 60.
Propargyl bromide adds to Ä…-chiral aldehydes with excellent
facial selectivity, but this leads to a mixture of allenyl and propar- 24. Stewart, F. H. C., J. Org. Chem. 1961, 26, 3604.
gyl alcohol (eq 48).81 It has been shown that Ä…-bromo acetonitrile 25. Pearl, I. A.; Dehn, W. M., J. Am. Chem. Soc. 1938, 60, 57; Pearl, I. A.,
J. Org. Chem. 1957, 22, 1229.
can react with various aldimines (eq 49). The reactions are carried
26. Chang, M.; Netzly, D. H.; Butler, L. G.; Lynn, D. G., J. Am. Chem. Soc.
out in anhydrous THF and unactivated tin was employed. The
1986, 108, 7858.
reaction is efficiently accelerated by addition of chlorotrimethyl-
27. Hodgson, H. H.; Leigh, E., J. Chem. Soc. 1939, 142, 1094.
silane.82
28. Dyson, G. M., Org. Synth., Coll. Vol. 1932, 1, 506.
H H
R2O CHO 29. Tanaka, H.; Taniguchi, M.; Kameyama, Y.; Monnin, M.; Sasaoka, M.;
Br
Shiroi, T.; Nagao, S.; Torii, S., Chem. Lett. 1990, 1867.
Sn, NH4Cl (aq sat)
N
30. Hoffmann, R. W., Angew. Chem., Int. Ed. Engl. 1982, 21, 555;
THF
O R1
Yamamoto, Y., Acc. Chem. Res. 1987, 20, 243.
65%
31. Mukaiyama, T.; Harada, T., Chem. Lett. 1981, 1527.
32. Nokami, J.; Otera, J.; Sudo, T.; Okawara, R., Organometallics 1983, 2,
H H H H
R2O R2O
191.
(48)
+
33. Boga, C.; Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A.,
N N
J. Organomet. Chem. 1988, 353, 177.
O R1 O R1
1:1
34. Petrier, C.; Einhorn, J.; Luche, J. L., Tetrahedron Lett. 1985, 26, 1449.
35. Schmid, W.; Whitesides, G. M., J. Am. Chem. Soc. 1991, 113, 6674.
36. Uneyama, K.; Matsuda, H.; Torii, S., Tetrahedron Lett. 1984, 25, 6017.
Br
N HN
37. Uneyama, K.; Kamaki, N.; Moriya, H.; Torii, S., J. Org. Chem. 1985,
N
(49)
50, 5396.
Sn, TMSCl, THF
38. (a) Coxon, J. M.; van Eyk, S. J.; Steel, P. J., Tetrahedron Lett. 1985, 26,
68%
6121. (b) Coxon, J. M.; van Eyk, S. J.; Steel, P. J., Tetrahedron 1989, 45,
N 1029.
39. Mandai, T.; Nokami, J.; Yano, T.; Yoshinaga, Y.; Otera, J., J. Org. Chem.
1984, 49, 172.
40. Nokami, J.; Tamaoka, T.; Ogawa, H.; Wakabayashi, S., Chem. Lett. 1986,
1. (a) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis;
541.
Butterworths: London, 1987. (b) Chemistry of Tin; Harrison, P. G., Ed.;
Chapman and Hall: New York, 1989. 41. Yamataka, H.; Nishikawa, K.; Hanafusa, T., Bull. Chem. Soc. Jpn. 1992,
65, 2145.
2. (a) Hudlicky, M. Reductions in Organic Synthesis; Horwood: Chichester,
1984. (b) Comprehensive Organic Synthesis 1991; 8, Chapters 1.1 4.8. 42. Kanagawa, Y.; Nishiyama, Y.; Ishii, Y., J. Org. Chem. 1992, 57, 6988.
A list of General Abbreviations appears on the front Endpapers
TIN 7
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