Asymmetric dehydration of beta-hydroxy esters and application to the syntheses of flavane derivatives

作者：Choi Eui Ta; Lee Min Hee; Kim Yongtae; Park Yong Sun^*

来源：Tetrahedron, 2008, 64(7): 1515-1522.

DOI：10.1016/j.tet.2007.11.026

• kinetic resolution
• asymmetric syntheses
• chiral catalyst
• flavonoids
• dehydration

Catalytic asymmetric dehydration of beta-aryl or alkyl substituted P-hydroxy esters via kinetic resolution has been investigated. A brief survey of 10 different chiral ligands is conducted to examine the effects of chiral ligand structure on selectivity of the dehydration. The kinetic resolution of a variety of rac-beta-hydroxy tert-butyl esters in the presence of prolinol chiral ligand 2 and BrZnCH2CO2-t-Bu can provide highly enantioenriched beta-hydroxy esters 14-21 with selectivity factors ranging from 11 to 66. Also, application of this asymmetric synthetic methodology to the preparation of enantioenriched flavane derivatives 25-29 is demonstrated.

• 出版日期2008-2-11