Highly Stereoselective [4+2] Cycloaddition of Azlactones to β,γ-Unsaturated α-Ketoesters Catalyzed by an Axially Chiral Guanidine Base

被引：49

作者：

Terada, Masahiro ^{[1
]}

Nii, Hiroyuki ^{[1
]}

机构：

[1] Tohoku Univ, Dept Chem, Grad Sch Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 06期

关键词：

amino sugar; asymmetric catalysis; cycloaddition; guanidine; organocatalysis; 1,3-DICARBONYL COMPOUNDS; ASYMMETRIC-SYNTHESIS; AMINO-ACIDS; DERIVATIVES; OXAZOL-5-(4H)-ONES; NITROALKENES; OXAZOLONES; AMINATION; ETHERS;

D O I：

10.1002/chem.201003015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Sweet catalysis! The enantio-and diastereoselective cycloaddition reaction of azlactones with β,γ-unsaturated α-ketoesters was demonstrated by taking advantage of the multiple reactive sites on the azlactone with the use of an axially chiral guanidine-base catalyst. The most likely reaction pathway involves three consecutive steps to provide a facile access to α-amino δ-lactones with a sugar framework in a highly stereoselective manner (see scheme). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1760 / 1763

页数：4

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