ENHANCEMENT OF ENANTIOSELECTIVITY IN INTRAMOLECULAR C-H INSERTION REACTIONS OF ALPHA-DIAZO BETA-KETO-ESTERS CATALYZED BY CHIRAL DIRHODIUM(II) CARBOXYLATES

被引：139

作者：

HASHIMOTO, S

WATANABE, N

SATO, T

SHIRO, M

IKEGAMI, S

机构：

[1] TEIKYO UNIV,FAC PHARMACEUT SCI,SAGAMIKO,KANAGAWA 19901,JAPAN

[2] SHIONOGI & CO LTD,SHIONOGI RES LAB,FUKUSHIMA KU,OSAKA 553,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 32期

关键词：

D O I：

10.1016/S0040-4039(00)60689-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselectivity in intramolecular C-H insertion reactions of alpha-diazo beta-keto esters catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-phenylalaninate] was found to be substantially improved by evaluation of the alkoxy group of the ester moiety. Cyclization of alpha-diazo beta-keto 2,4-dimethyl-3-pentyl esters was promoted by this catalyst to afford, after a removal of the ester group, optically active 3-substituted cyclopentanones of up to 76% ee.

引用

页码：5109 / 5112

页数：4

共 28 条

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