Kinetic Resolution of β-Alkenyl-, β-Alkynyl- and β-Flavenyl-Substituted β-Hydroxy Esters in Asymmetric Dehydration

被引：14

作者：

Lee, Min Hee ^{[1
]}

Choi, Eui Ta ^{[1
]}

Kim, Dajung ^{[1
]}

Lee, Yoon Min ^{[1
]}

Park, Yong Sun ^{[1
]}

机构：

[1] Konkuk Univ, Dept Chem, Biomol Informat Ctr, Seoul 143701, South Korea

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 33期

关键词：

Kinetic resolution; Asymmetric catalysis; Dehydration; Chiral ligands; Flavonoids;

D O I：

10.1002/ejoc.200800807

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric dehydration of beta-alkenyl- or alkynyl-substituted beta-hydroxy esters by kinetic resolution has been investigated with five different chiral ligands 3-7. The kinetic resolution of a variety of racemic P-hydroxy tert-butyl esters in the presence of a prolinol chiral ligand and BrZnCH(2)CO(2)tBu provided highly enantio-enriched beta-hydroxy esters 9-22 with selectivity factors ranging from 11 to 59. In addition, the application of this asymmetric synthetic methodology to the preparation of enantio-enriched flavene derivatives 23-29 is demonstrated. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

引用

页码：5630 / 5637

页数：8

共 25 条

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