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Activation of Hemiaminal Ethers by Chiral Brønsted Acids for Facile Access to Enantioselective Two‐Carbon Homologation Using Enecarbamates
Author(s) -
Terada Masahiro,
Machioka Kyoko,
Sorimachi Keiichi
Publication year - 2009
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.200805385
Subject(s) - hemiaminal , enantioselective synthesis , chemistry , brønsted–lowry acid–base theory , phosphoric acid , organic chemistry , catalysis
Abstract An enriching experience : Chiral phosphoric acids have been used to catalyze the title transformation for aromatic and aliphatic hemiaminal ethers. The process affords the corresponding products in good to high enantioselectivity (see scheme; Boc= tert ‐butoxycarbonyl, G=aromatic group). The method enables facile access to highly enantioenriched 1,3‐diamine derivatives.