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
收藏
页码：5630 / 5637
页数：8
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