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Asymmetric Mannich Reaction of Imines Derived from Aliphatic and Aromatic Aldehydes Catalyzed by Diarylprolinol Silyl Ether
Author(s) -
Urushima Tatsuya,
Ishikawa Hayato,
Hayashi Yujiro
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101077
Subject(s) - mannich reaction , silylation , catalysis , ether , chemistry , silyl ether , organic chemistry
Anti Mannich, try this! A direct asymmetric Mannich reaction catalyzed by a diarylprolinol silyl ether was developed to afford the anti ‐Mannich product with excellent enantioselectivity. Imines derived from both aliphatic and aromatic aldehydes were successfully used to obtain the synthetically important β‐amino aldehydes (see scheme; Ts=tosyl). The reaction can also be performed in the presence of water.