Modular synthesis of chiral N-protected β-seleno amines and amides via cleavage of 2-oxazolidinones and application in palladium-catalyzed asymmetric allylic alkylation

被引：16

作者：

Sehnem, Jasquer A. ^{[1
]}

Vargas, Fabricio ^{[1
]}

Milani, Priscila ^{[1
]}

Nascimento, Vanessa ^{[1
]}

Braga, Antonio L. ^{[1
]}

机构：

[1] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil

来源：

SYNTHESIS-STUTTGART | 2008年 / 8卷 / 08期

关键词：

beta-seleno amines; allylic alkylation; oxazolidinone ring-opening; asymmetric catalysis;

D O I：

10.1055/s-2008-1042938

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A set of chiral beta-seleno amines have been efficiently synthesized via the ring-opening reaction of chiral N-acyl oxazolidinones by selenium nucleophiles. These compounds could be transformed into beta-seleno amides by reaction with acid chlorides. The present method is applicable to the synthesis of beta-chalcogeno amides containing selenium, sulfur and tellurium atoms in good yields. Additionally, these new compounds were evaluated as ligands in the palladium-catalyzed asymmetric allylic alkylation, giving the corresponding alkylated products in up to 98% ee.

引用

页码：1262 / 1268

页数：7

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