Efficient synthesis of chiral β-seleno amides via ring-opening reaction of 2-oxazolines and their application in the palladium-catalyzed asymmetric allylic alkylation

被引：102
作者：
Braga, AL [1 ]
Vargas, F [1 ]
Sehnem, JA [1 ]
Braga, RC [1 ]
机构：
[1] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 22期
关键词：
D O I：
10.1021/jo051451a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHIC] A set of chiral beta-seleno amides have been efficiently synthesized via the ring-opening reaction of chiral 2-oxazolines by selenium nucleophiles. The present method is applicable to the synthesis of beta-seleno amides containing thioether, alcohol, and ether moieties in good yields. As an application, the synthesis of a selenocysteine derivative has been accomplished. Additionally, these new compounds were evaluated in the palladium-catalyzed asymmetric allylic alkylation, giving the alkylated products in up to 98% ee.
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页码：9021 / 9024
页数：4
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