Mechanistic insights into the factors determining exo-endo selectivity in the Lewis acid-catalyzed Diels-Alder reaction of 1,3-dienes with 2-cycloalkenones

被引：56

作者：

Ge, M ^{[1
]}

Stoltz, BM ^{[1
]}

Corey, EJ ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 13期

关键词：

D O I：

10.1021/ol0060026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We adduce evidence that the asynchronous, Lewis acid-catalyzed Diets-Alder reaction of 2-cycloalkenones with nonsimple alpha,beta-enones can proceed via transition states in which the 1,3-diene subunit is skewed, i.e., nonplanar, with profound effects on the ratio of exo and endo addition products.

引用

页码：1927 / 1929

页数：3

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