A SIMPLE AND HIGHLY STEREOSELECTIVE ROUTE TO E-ALPHA,BETA-UNSATURATED ALDEHYDES

被引：60

作者：

BELLASSOUED, M

MAJIDI, A

机构：

[1] Université Pierre et Marie Curie, Laboratoire de Synthèse Organométallique, CNRS UA 408, 75252 Paris Cedex 05, 4, Place Jussieu

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 09期

关键词：

D O I：

10.1021/jo00061a027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Zinc bromide mediated reaction of alpha,alpha-bis(trimethylsilyl)-tert-butylacetaldimine (3) with a wide range of aldehydes takes place under mild conditions and affords the corresponding alpha,beta-unsaturated aldehydes in good yields and with very high E stereoselectivity (>98%). This procedure is successfully applied to the preparation of intermediates for retinoid and natural product synthesis.

引用

页码：2517 / 2522

页数：6

共 55 条

[1] AKGUN E, 1984, SYNTHESIS-STUTTGART, V3, P227
[2] ARENS JF, 1960, ADV ORG CHEM, V2, P157
[3] CUMULATED YLIDES .7. A STEREOSELECTIVE SYNTHETIC METHOD FOR (Z)-ALPHA,BETA-UNSATURATED ALDEHYDES
BESTMANN, HJ
ROTH, K
ETTLINGER, M
[J]. CHEMISCHE BERICHTE-RECUEIL, 1982, 115 (01): : 161 - 171
[4] BESTMANN HJ, 1977, TETRAHEDRON LETT, P121
[5] OLEFIN SYNTHESIS WITH ORGANIC PHOSPHONATE CARBANIONS
BOUTAGY, J
THOMAS, R
[J]. CHEMICAL REVIEWS, 1974, 74 (01) : 87 - 99
[6] The preparation of unsymmetrical secondary aliphatic ammes
Campbell, KN
Sommers, AH
Campbell, BK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 : 82 - 84
[7] CHATTHA MS, 1971, TETRAHEDRON LETT, P1419
[8] ME5CU3LI2 - A REAGENT FOR CONJUGATE METHYLATION OF ALPHA,BETA-UNSATURATED ALDEHYDES
CLIVE, DLJ
FARINA, V
BEAULIEU, PL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) : 2572 - 2582
[9] CLOUX R, 1984, HELV CHIM ACTA, V67, P170
[10] SYNTHESIS OF DIENALS BY CONDENSATION OF CARBONYL-COMPOUNDS WITH A NEW REAGENT, THE 4-LITHIO-1-TRIMETHYLSILOXYBUTADIENE
CONTRERAS, B
DUHAMEL, L
PLE, G
[J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (19) : 2983 - 2990

← 1 2 3 4 5 6 →