Phosphine-catalyzed cycloadditions of allenic ketones: New substrates for nucleophilic catalysis

被引：135

作者：

Wallace, Debra J. ^{[1
]}

Sidda, Rachel L. ^{[1
]}

Reamer, Robert A. ^{[1
]}

机构：

[1] Merck Sharp & Dohme Res Labs, Dept Proc Res, Hoddesdon EN11 9BU, Herts, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 03期

关键词：

D O I：

10.1021/jo062170l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of phosphine-catalyzed cycloaddition reactions of allenic ketones have been studied, extending the scope of these processes from the more widely used 2,3-butadienoates to allow access to a number of synthetically useful products. Reaction of allenyl methyl ketone 4 with exo-enones afforded spirocyclic compounds in good regioselectivity and promising enantioselectivity via a [2 + 3] cycloaddtion. Aromatic allenyl ketones undergo a phosphine-promoted dimerization to afford functionalized pyrans, leading to a formal [2 + 4] Diels-Alder product, but did not react in the [2 + 3] cycloaddition. The results from other reactions that had found utility with 2,3-butadienoates are also reported.

引用

页码：1051 / 1054

页数：4

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