ENDO-2-METHYL-BICYCLO[2.2.1]HEPT-5-ENYL ETHYL KETONE - AN USEFUL AND HIGHLY STEREOSELECTIVE SYNTHON FOR ALDOL REACTIONS

被引：12

作者：

AHMAR, M ^{[1
]}

BLOCH, R ^{[1
]}

MANDVILLE, G ^{[1
]}

ROMAIN, I ^{[1
]}

机构：

[1] UNIV PARIS 11, INST CHIM MOLEC ORSAY,CNRS,CARBOCYCLES LAB,BAT 420, F-91405 ORSAY, FRANCE

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(00)92225-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An excellent aldehyde diastereofacial selectivity has been observed during the aldol condensation between the lithium enolate of endo-2-methyl-bicyclo[2.2.1]-hept-5-enyl ethyl ketone 1 and a variety of alpha-methyl chiral aldehydes. 2-Aryl- and 2-vinyl-propionaldehyde gave rise to the predicted syn, syn "Felkin-Anh" diastereoisomers. In contrast beta-alkoxy or beta-silyloxy alpha-methyl aldehydes lead to the syn, anti aldols arising from an apparent chelation control.

引用

页码：2501 / 2504

页数：4

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