Enantioselective Diels-Alder reaction of acyclic enones catalyzed by allo-threonine-derived chiral oxazaborolidinone

被引：15

作者：

Singh, RS ^{[1
]}

Harada, T

机构：

[1] Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 6068585, Japan

[2] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 16期

关键词：

asymmetric catalysis; asymmetric synthesis; boron; cycloaddition; Lewis acids;

D O I：

10.1002/ejoc.200500356

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An allo-threonine-derived O-(p-biphenylcarbonyloxy)-B-phenyl-oxazaborolidinone is demonstrated to be a powerful and highly enantioselective Lewis acid catalyst for the enantioselective Diels-Alder reaction of simple acyclic enone dienophiles, expanding the scope of ketone dienophiles and dienes. With 10-20 mol% of the catalyst, the Diels-Alder adducts are obtained with up to 94% ee and high endo selectivity. The catalyst exhibits a high activity in the reaction with the less reactive beta-substituted dienophiles and the less reactive 1,3-cycohexadiene and 1,3-butadiene derivatives. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

引用

页码：3433 / 3435

页数：3

共 24 条

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