Formal intermolecular 4+4 approach to cyclooctanoids: 4+3 capture of the Nazarov oxyallyl intermediate with simple 1,3-dienes

被引：79

作者：

Wang, Y ^{[1
]}

Schill, BD ^{[1
]}

Arif, AM ^{[1
]}

West, FG ^{[1
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 15期

关键词：

D O I：

10.1021/ol034985b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Simple 1,4-dien-3-ones and 1,3-dienes react in the presence of BF3.OEt2 via a domino Nazarov electrocyclization/intermolecular [4 + 3]-cycloaddition sequence to furnish keto-bridged cyclooctenes in good yield. Most cases showed high diastereofacial selectivity and/or endo/exo selectivity, and surprising levels of regioselectivity were observed when isoprene was used as the diene partner.

引用

页码：2747 / 2750

页数：4

共 38 条

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[2]

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