Metallophosphite-induced nucleophilic acylation of α,β-unsaturated amides:: Facilitated catalysis by a diastereoselective retro [1,4] Brook rearrangement

被引：53

作者：

Nahm, MR ^{[1
]}

Linghu, X ^{[1
]}

Potnick, JR ^{[1
]}

Yates, CM ^{[1
]}

White, PS ^{[1
]}

Johnson, JS ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 16期

关键词：

acylation; asymmetric catalysis; rearrangement; umpolung;

D O I：

10.1002/anie.200462795

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Intermolecular alkene acylation reactions between acyl silanes and α,β-unsaturated amides with metallophosphite catalysis afford α-silyl-γ-ketoamides with high diastereoselectivities (see scheme). These can be converted into the corresponding γ-ketoamides and α-bromo-γ-ketoamides. Asymmetric catalysis of the acylation delivers the γ-ketoamide in the highest enantioselectivity yet reported for an intermolecular Stetter-type reaction. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2377 / 2379

页数：3

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