EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF ALLYLSILANES BY WITTIG OLEFINATION OF ALPHA-SILYLALDEHYDES

被引：33

作者：

BHUSHAN, V ^{[1
]}

LOHRAY, BB ^{[1
]}

ENDERS, D ^{[1
]}

机构：

[1] RHEIN WESTFAL TH,INST ORGAN CHEM,PROF PIRLET STR 1,D-52074 AACHEN,GERMANY

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 32期

关键词：

D O I：

10.1016/S0040-4039(00)60677-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylsilanes 2 of high enantiomeric purity (ee = 90 - greater-than-or-equal 98 %) are prepared in good yields from optically active alpha-silylaldehydes 1 via Wittig olefination with various alkylidene triphenylphosphoranes in high E:Z selectivities (90:10 - 97:3) and without racemization of the alpha-silylaldehydes. The latter are easily obtained from simple aldehydes and silylating agents employing the SAMP/RAMP-hydrazone method.

引用

页码：5067 / 5070

页数：4

共 44 条

[1] Bassindale A., 1991, FRONTIERS ORGANOSILI
[2] Colvin E. W., 1988, SILICON REAGENTS ORG
[3] Colvin E. W., 1981, SILICON ORGANIC SYNT
[4] SUPERACID CATALYSIS OF THE ADDITION OF ALLYSILANES TO CARBONYL-COMPOUNDS
DAVIS, AP
JASPARS, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (17) : 1176 - 1178
[5] REGIOSELECTIVE, DIASTEREOSELECTIVE, AND ENANTIOSELECTIVE SYNTHESIS OF VICINAL DIOLS VIA ALPHA-SILYL KETONES
ENDERS, D
NAKAI, S
[J]. HELVETICA CHIMICA ACTA, 1990, 73 (07) : 1833 - 1836
[6] ASYMMETRIC SYNTHESIS VIA METALATED CHIRAL HYDRAZONES - ENANTIOSELECTIVE ALKYLATION OF CYCLIC-KETONES AND ALDEHYDES
ENDERS, D
EICHENAUER, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (08): : 2933 - 2960
[7] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-TRIALKYLSILYL KETONES AND ALDEHYDES
ENDERS, D
LOHRAY, BB
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (04): : 351 - 352
[8] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALDOL REACTIONS VIA ALPHA-SILYL KETONES, ASYMMETRIC-SYNTHESIS OF THE AGGREGATION PHEROMONE SITOPHILURE
ENDERS, D
LOHRAY, BB
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (04): : 581 - 583
[9] REGIOSELECTIVE, DIASTEREOSELECTIVE, AND ENANTIOSELECTIVE SYNTHESIS OF VIC-DIOLS VIA ALPHA-SILYL KETONES ACCORDING TO THE SAMP/RAMP HYDRAZONE METHOD
ENDERS, D
NAKAI, S
[J]. CHEMISCHE BERICHTE, 1991, 124 (01) : 219 - 226
[10] ENDERS D, UNPUB CHEM BER

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