Unusual diastereoselectivity in intramolecular Diels-Alder reactions of substituted 3,5-hexadienyl acrylates. Preference for a boatlike structure of the six-atom tether due to ester overlap

被引：38

作者：

Jung, ME ^{[1
]}

Huang, A ^{[1
]}

Johnson, TW ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 13期

关键词：

D O I：

10.1021/ol000104e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermolysis of the 3,5-hexadienyl acrylates (a) proceeds via the transition state E in which the connecting chain adopts a boatlike conformation due to a preference for maintaining ester overlap to afford the products b with good diastereoselectivity.

引用

页码：1835 / 1837

页数：3

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