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High Substrate/Catalyst Organocatalysis by a Chiral Brønsted Acid for an Enantioselective Aza‐Ene‐Type Reaction
Author(s) -
Terada Masahiro,
Machioka Kyoko,
Sorimachi Keiichi
Publication year - 2006
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.200503477
Subject(s) - enantioselective synthesis , organocatalysis , ene reaction , catalysis , substrate (aquarium) , chemistry , enantiomeric excess , brønsted–lowry acid–base theory , enantiomer , organic chemistry , biology , ecology
Lowering the load : A very small amount of a binaphthol‐derived monophosphoric acid organocatalyst accelerates an aza‐ene‐type reaction of N ‐benzoylimines with enecarbamates to provide β‐aminoimines with high enantiomeric purity. This catalysis with a high substrate/catalyst(S/C) ratio provides a practical route to 1,3‐diamine derivatives of synthetic and biological importance.