Predicting the diastereoselectivity of Rh-mediated intramolecular C-H insertion

被引：133

作者：

Taber, DF

You, KK

Rheingold, AL

机构：

[1] Dept. of Chemistry and Biochemistry, University of Delaware, Newark

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1996年 / 118卷 / 03期

关键词：

D O I：

10.1021/ja9515213

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rhodium-mediated cyclization of the alpha-diazo ester 1 proceeds with high diastereoselectivity, to give the trisubstituted cyclopentane 5. A computational model (ZINDO and Molecular Mechanics) based on our current mechanistic understanding of the reaction is presented. This model correctly predicts the dominant diastereomer from the cyclization of 1 and the eight (Table 2) other alpha-diazo esters studied thus far.

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页码：547 / 556

页数：10

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