Tandem carbon-carbon bond constructions via catalyzed cyanation/Brook rearrangement/C-acylation reactions of acylsilanes

被引：48

作者：

Xin, LH ^{[1
]}

Nicewicz, DA ^{[1
]}

Johnson, JS ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 17期

关键词：

D O I：

10.1021/ol0263649

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem nucleophile-catalyzed cyanation/Brook rearrangement/C-acylation has been developed. Phase transfer cocatalysts facilitate cyanide-catalyzed reactions between acylsilanes and cyanoformates to afford protected tertiary carbinol products, A catalytic cycle is proposed involving cyanation of an acylsilane, [1,2]-Brook rearrangement, and C-acylation of the derived carbanion by a cyanoformate ester. The reaction offers an efficient method for the preparation of functionalized, unsymmetrical malonic acid derivatives.

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页码：2957 / 2960

页数：4

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