Regio- and stereocontrol elements in Rh(II)-catalyzed intramolecular C-H insertion of α-diazo-α-(phenylsulfonyl)acetamides

被引：59

作者：

Yoon, CH ^{[1
]}

Zaworotko, MJ ^{[1
]}

Moulton, B ^{[1
]}

Jung, KW ^{[1
]}

机构：

[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 22期

关键词：

D O I：

10.1021/ol016647l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Intramolecular C-H insertion reaction of alpha -diazo-alpha-(phenylsulfonyl)aceta rn ides proceeded with high regio- and stereoselectivities to afford highly functionalized gamma -lactams predominantly or exclusively. The high regioselectivity was attributed to the use of the phenylsulfonyl moiety, which altered electron density at the carbenoid center and exerted a steric effect during the insertion reaction. Also described herein are three control elements to determine regioselectivity, which are amide conformational, stereoelectronic, and substituent effects.

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页码：3539 / 3542

页数：4

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