Metalated nitriles: Cation-controlled cyclizations

被引：13

作者：

Fleming, Fraser F. ^{[1
]}

Wei, Yunjing ^{[1
]}

Liu, Wang ^{[1
]}

Zhang, Zhiyu ^{[1
]}

机构：

[1] Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 14期

关键词：

D O I：

10.1021/ol071084k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Judicious choice of cation allows the selective cyclization of substituted gamma-hydroxynitriles to trans- or cis-decalins and trans- or cis-bicyclo[5.4.0]undecanes. The stereoselectivities are consistent with deprotonations generating two distinctly different metalated nitriles: an internally coordinated nitrile anion with BuLi, and a C-magnesiated nitrile with i-PrMgCl. Employing cations to control the geometry of metalated nitriles permits stereodivergent cyclizations with complete control over the stereochemistry of the quaternary, nitrile-bearing carbon.

引用

页码：2733 / 2736

页数：4

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