Lewis acid-catalyzed Michael addition reactions of N-Boc-2-silyloxypyrroles to 3-acryloyl-2-oxazolidinone

被引：29

作者：

Suga, Hiroyuki ^{[1
]}

Takemoto, Haruka ^{[1
]}

Kakehi, Akikazu ^{[1
]}

机构：

[1] Shinshu Univ, Fac Engn, Dept Chem & Mat Engn, Wakasato, Nagano 3808553, Japan

来源：

HETEROCYCLES | 2007年 / 71卷 / 02期

关键词：

D O I：

10.3987/COM-06-10966

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Among several Lewis acids examined, Sc(OTf)(3) (10 mol%) was found to be the most effective catalyst to promote a Michael addition reaction of N-Boc-2-(tert-butyldimethylsilyloxy)pyrrole to 3-acryloyl-2-oxazolidinone. A slow addition of the 2-silyloxypyrrole in the presence of 1,1,1,3,3,3-hexafluoro-2-propanol (5 equiv.) at -25 degrees C were needed to obtain good yield (77 - 80%). The asymmetric version of the reaction could be performed with good enantioselectivity (up to 82% ee) by using the chiral Sc(III) catalyst (10 mol%), which was prepared from 2,6-bis[(4S)-4-isopropyl-2-oxazolin-2-yl]pyridine and Sc(OTf)(3), in reasonable yield (60 - 70%).

引用

页码：361 / 371

页数：11

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