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A Simple Chiral Cu(II) Complex as an Effective Phase‐Transfer Catalyst for the Enantioselective Alkylation of Dissymmetric Glycinate Ketimines
Author(s) -
Bafqiren Hanane,
Zouihri Hafid,
Gmouh Said,
Jamal Eddine Jamal
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22529
Subject(s) - chemistry , enantioselective synthesis , alkylation , catalysis , phase (matter) , combinatorial chemistry , simple (philosophy) , organic chemistry , philosophy , epistemology
Catalytic asymmetric benzylation of a dissymmetric tert ‐butylglycinate ketimine, incorporating 1‐naphthyl and phenyl groups as the Schiff base substituents, under phase‐transfer conditions was investigated. It was interesting to note that the sense of asymmetric induction of the alkylation of Z ‐imine stereoisomer is opposite to that of the corresponding E stereoisomer with a similar degree of enantioselectivity . More interestingly, the chiral Cu(II) complex of the Schiff base derived from ( R )‐2‐phenylglycinol and 2‐hydroxy‐1‐naphthaldehyde was found to catalyze the same reaction under solid‐liquid conditions with comparable enantioselectivity (up to 60% ee ) with respect to known cinchona alkaloid catalysts. The solvent/base‐system parameter was shown to control the optimal catalytic activity . Chirality 27:944–950, 2015 . © 2015 Wiley Periodicals, Inc.