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Enantioselective Strecker Reaction Catalyzed by an Organocatalyst Lacking a Hydrogen‐Bond‐Donor Function
Author(s) -
Negru Mihaela,
Schollmeyer Dieter,
Kunz Horst
Publication year - 2007
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.200703179
Subject(s) - enantioselective synthesis , chemistry , strecker amino acid synthesis , hydrogen cyanide , catalysis , hydrogen bond , organocatalysis , organic chemistry , molecule
Self‐activation : N ‐Glycosyl imines A of planar chiral [2.2]paracyclophane carbaldehydes act as efficient enantioselective organocatalysts for the Strecker synthesis of α‐amino nitriles, although they do not contain a hydrogen‐bond donor or a Brønsted acid function. They activate themselves by deprotononation of hydrogen cyanide and catalyze the formation of both aliphatic and aromatic amino nitriles with high enantioselctivity.