ASYMMETRIC SYN-SELECTIVE MICHAEL ADDITION OF ENOLATES TO CHIRAL 8-PHENYLMENTHYLOXY VINYL CHROMIUM CARBENE COMPLEXES

被引：58

作者：

BARLUENGA, J ^{[1
]}

MONTSERRAT, JM ^{[1
]}

FLOREZ, J ^{[1
]}

GARCIAGRANDA, S ^{[1
]}

MARTIN, E ^{[1
]}

机构：

[1] UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33006 OVIEDO,SPAIN

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 1995年 / 1卷 / 04期

关键词：

ASYMMETRIC SYNTHESES; ENOL ETHERS; FISCHER CARBENES; MICHAEL ADDITIONS; SYN DIASTEREOSELECTIVITY;

D O I：

10.1002/chem.19950010407

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Michael addition reactions of ketone and ester lithium enolates to optically active Fischer vinylcarbene complexes derived from (-)-8-phenylmenthol take place with high syn selectivity and high levels of asymmetric induction. The initial Michael adducts can be further elaborated through diastereoselective addition of organometallic reagents to ketones and aldol reactions. Removal of the metal fragment and chiral auxiliary group leads to cyclic enol ethers with three or five contiguous stereogenic centers and of high enantiomeric purity.

引用

页码：236 / 242

页数：7

共 69 条

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