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Highly Enantioselective Opening of Cyclic meso ‐Anhydrides to Isopropyl Hemiesters with Diisopropoxytitanium TADDOLates
Author(s) -
Seebach Dieter,
Jaeschke Georg,
Wang Yan Ming
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199523951
Subject(s) - enantioselective synthesis , chemistry , isopropyl , ligand (biochemistry) , kinetic resolution , enantiomer , alkoxide , stereochemistry , ring (chemistry) , hydrolysis , organic chemistry , catalysis , receptor , biochemistry
The Lewis acid mediated transfer of an alkoxide ligand from the chiral ligand sphere of 1 facilitates the highly enantioselective ring‐opening of cyclic C S ‐symmetric anhydrides 2 to the corresponding hemiesters 3 with enantiomer ratios up to 99:1. This ability to transfer ligands could make 1 an organometallic alternative to hydrolytic enzymes, as the differntiation of enantiotopic functional groups in meso compounds and the resolution of racemic substrates should be possible.