Cyanide-catalyzed additions of acyl phosphonates to aldehydes: A new acyl donor for benzoin-type reactions

被引：68

作者：

Bausch, CC ^{[1
]}

Johnson, JS ^{[1
]}

机构：

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 09期

关键词：

benzoin condensation; cyanide catalysis; ketones; phosphate ester; rearrangement; umpolung;

D O I：

10.1002/adsc.200505097

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Acyl phosphonates have been utilized as new acyl donors for cyanide-catalyzed benzoin-type reactions. Cyanation of acyl phosphonates, followed by a [1,2]-phosphoryl migration generates the active acyl anion intermediate. The presumed (cyano)phosphate anion reacts with a variety of aryl aldehydes to yield phosphate ester-protected, unsymmetrical benzoins in good to excellent yields. The unsymmetrical benzoin product can be obtained after deprotection of the phosphate ester with an aqueous amine solution.

引用

页码：1207 / 1211

页数：5

共 16 条

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