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Direct Organocatalytic Mannich Reaction of Acetaldehyde: An Improved Catalyst and Mechanistic Insight from a Computational Study
Author(s) -
Hayashi Yujiro,
Okano Tsubasa,
Itoh Takahiko,
Urushima Tatsuya,
Ishikawa Hayato,
Uchimaru Tadafumi
Publication year - 2008
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.200802073
Subject(s) - acetaldehyde , chemistry , catalysis , mannich reaction , toluene , organocatalysis , organic chemistry , reaction mechanism , amine gas treating , combinatorial chemistry , enantioselective synthesis , ethanol
A chiral diaryl prolinol silyl ether organocatalyst with an acid is used for the direct catalytic asymmetric Mannich reaction of acetaldehyde and imines. N ‐Benzoyl‐, N‐tert ‐butoxycarbonyl‐, and N ‐toluene‐4‐sulfonylimines can be employed to produce synthetically useful β‐amino aldehydes in good yields and with excellent enantioselectivity (see scheme). The reaction mechanism was investigated quantum‐mechanically.