Stereoselective synthesis of highly substituted cyclopentenones through [4+1] annulations of trialkylsilyl vinyl ketenes with α-benzotriazolyl organolithium compounds

被引：46

作者：

Davie, CP ^{[1
]}

Danheiser, RL ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 36期

关键词：

annulation; azoles; cyclopentenones; electrocyclic reactions; ketenes;

D O I：

10.1002/anie.200501579

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Closing the ring: Highly functionalized cyclopentenones are prepared by the reaction of readily available metalated benzotriazole derivatives with trialkylsilyl vinyl ketenes (see scheme; Z = heteroatom substituent). Dienolate intermediates are generated which form the five-membered ring. Most transformations proceed with high stereoselectivity by a (Chemical Equation Presented) mechanism believed to involve stereospecific 4π-electrocyclic ring closure. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

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页码：5867 / 5870

页数：4

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