REMARKABLE INCREASE IN THE DIASTEREOFACIAL SELECTIVITY OF THE ADDITION OF BETA-METHYL ALPHA-(ALKOXY)ALLYLSTANNANE TO ALDEHYDES - SUBSTITUENT EFFECTS ON DIASTEREOFACIAL SELECTIVITY

被引：32

作者：

GUNG, BW

SMITH, DT

WOLF, MA

机构：

[1] Department of Chemistry, Miami University, Oxford

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(00)71205-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several new chiral allylstannanes were prepared and reacted with aldehydes. Excellent diastereofacial selectivity was observed for the reactions of allylstannane 1 with aldehydes in the presence of BF3.Et2O. This is in contrast to the results from other allystannanes which do not bear a beta-methyl group. These observations were rationalized based on a combination of steric and electronic effects.

引用

页码：13 / 16

页数：4

共 23 条

[1] STEREOCHEMISTRY OF ALLYLMETAL ALDEHYDE CONDENSATIONS .2. ALLYLSTANNANES
DENMARK, SE
WEBER, EJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (25) : 7970 - 7971
[2] HYDROSTANNATION OF BICYCLO [3.1.0] HEX-2-ENE - SYNTHESIS AND IDENTIFICATION OF DIASTEREOISOMERIC 4-METHYL-3-TRIMETHYLSTANNYLCYCLOPENTENES AND 5-METHYL-3-TRIMETHYLSTANNYLCYCLOPENTENES
DUMARTIN, G
QUINTARD, JP
PEREYRE, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 252 (01) : 37 - 46
[3] THE CRYSTAL-STRUCTURE OF TRIPHENYLALLYLTIN
GANIS, P
FURLANI, D
MARTON, D
TAGLIAVINI, G
VALLE, G
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 293 (02) : 207 - 212
[4] GUNG BG, 1991, UNPUB TETRAHEDRON LE, V32
[5] ACYCLIC STEREOSELECTION .4. ASSIGNMENT OF STEREOSTRUCTURE TO BETA-HYDROXYCARBONYL COMPOUNDS BY C-13 NUCLEAR MAGNETIC-RESONANCE
HEATHCOCK, CH
PIRRUNG, MC
SOHN, JE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) : 4294 - 4299
[6] STERIC MODELS FOR STEREOSELECTIVITY OF NITRILE OXIDE CYCLOADDITIONS TO CHIRAL ALKENES
HOUK, KN
DUH, HY
WU, YD
MOSES, SR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (10) : 2754 - 2755
[7] STEREOSELECTIVE NITRILE OXIDE CYCLO-ADDITIONS TO CHIRAL ALLYL ETHERS AND ALCOHOLS - THE INSIDE ALKOXY EFFECT
HOUK, KN
MOSES, SR
WU, YD
RONDAN, NG
JAGER, V
SCHOHE, R
FRONCZEK, FR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (13) : 3880 - 3882
[8] CHEMISTRY OF CARBANIONS .23. USE OF METAL-COMPLEXES TO CONTROL ALDOL CONDENSATION
HOUSE, HO
CRUMRINE, DS
TERANISH.AY
OLMSTEAD, HD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) : 3310 - 3324
[9] JONES AB, 1989, J ORG CHEM, V54, P19
[10] CHELATION CONTROLLED DIASTEREOFACIAL SELECTIVITY IN CROTYLTRI-N-BUTYLSTANNANE ADDITIONS TO ALPHA-ALKOXYALDEHYDES
KECK, GE
BODEN, EP
[J]. TETRAHEDRON LETTERS, 1984, 25 (18) : 1879 - 1882

← 1 2 3 →