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Practical Asymmetric Synthesis of Vicinal Diamines through the Catalytic Highly Enantioselective Alkylation of Glycine Amide Derivatives
Author(s) -
Ooi Takashi,
Sakai Daiki,
Takeuchi Mifune,
Tayama Eiji,
Maruoka Keiji
Publication year - 2003
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.200352658
Subject(s) - enantioselective synthesis , vicinal , alkylation , chemistry , amide , glycine , catalysis , bromide , combinatorial chemistry , side chain , stereochemistry , organic chemistry , amino acid , biochemistry , polymer
Phase‐transfer catalysis (PTC) by a designer chiral quaternary ammonium bromide facilitated the direct, highly enantioselective introduction of a wide variety of substituents including cycloalkyl side chains at the α position of the prochiral glycine amide derivative 1 . A general, practical procedure for the asymmetric synthesis of structurally diverse monosubstituted vicinal diamines of type 2 is presented. Dpm=diphenylmethyl.