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Kinetic Resolution of β‐Alkenyl‐, β‐Alkynyl‐ and β‐Flavenyl‐Substituted β‐Hydroxy Esters in Asymmetric Dehydration
Author(s) -
Lee Min Hee,
Choi Eui Ta,
Kim Dajung,
Lee Yoon Min,
Park Yong Sun
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800807
Subject(s) - chemistry , kinetic resolution , dehydration , enantioselective synthesis , selectivity , ligand (biochemistry) , catalysis , stereochemistry , resolution (logic) , chiral ligand , organic chemistry , artificial intelligence , computer science , biochemistry , receptor
Catalytic asymmetric dehydration of β‐alkenyl‐ or alkynyl‐substituted β‐hydroxy esters by kinetic resolution has been investigated with five different chiral ligands 3 – 7 . The kinetic resolution of a variety of racemic β‐hydroxy tert ‐butyl esters in the presence of a prolinol chiral ligand and BrZnCH 2 CO 2 t Bu provided highly enantio‐enriched β‐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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)