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Organocatalytic Enantioselective Strecker Reaction of Imines Containing a Thiazole Moiety by Using a Cinchona‐Based Squaramide Catalyst
Author(s) -
He HaiXiao,
Du DaMing
Publication year - 2014
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.201402764
Subject(s) - squaramide , chemistry , enantioselective synthesis , strecker amino acid synthesis , moiety , cinchona , organocatalysis , organic chemistry , catalysis , thiazole , cinchonidine , combinatorial chemistry
An organocatalytic enantioselective Strecker reaction was developed for the synthesis of α‐amino nitriles that contain a thiazole moiety by using a cinchona‐based squaramide catalyst. The corresponding products were obtained in good to excellent yields (up to 99 %) with excellent enantioselectivities (up to 98 % ee ) by starting from aromatic‐substituted imines. In addition, two trifunctional squaramides with amino acid residues were synthesized, and good enantioselectivities (up to 89 % ee ) were achieved when they were employed in the model reaction.