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Enantioselective Preparation of β,β‐Disubstituted α‐Methylenepropionates by MAO Promotion of the Zinc Schlenk Equilibrium
Author(s) -
Goldsmith Paul J.,
Teat Simon J.,
Woodward Simon
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200463028
Subject(s) - enantioselective synthesis , yield (engineering) , methylaluminoxane , zinc , chemistry , sn2 reaction , organic chemistry , catalysis , materials science , metallurgy , polymer , metallocene , polymerization
The zinc Schlenk equilibrium , little used since it was first described in 1966, has been promoted through the addition of methylaluminoxane (MAO) to maximize the yield of ZnR 2 from deleterious RZnCl by‐products. This process allows an S N 2′‐addition approach to the preparation of chiral β,β‐disubstituted α‐methylenepropionates with high enantioselectivity (see scheme).