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The Proline‐Catalyzed Double Mannich Reaction of Acetaldehyde with N ‐Boc Imines
Author(s) -
Chandler Carley,
Galzerano Patrizia,
Michrowska Anna,
List Benjamin
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.200806049
Subject(s) - acetaldehyde , mannich reaction , chemistry , diastereomer , catalysis , proline , double bond , organic chemistry , medicinal chemistry , stereochemistry , amino acid , biochemistry , ethanol
Double‐cross : Proline catalyzes the double Mannich reaction of acetaldehyde with N ‐Boc imines in excellent yields (up to 99 %; Boc= tert ‐butoxycarbonyl) and close to perfect diastereo‐ and enantioselectivities. Depending on the choice of catalysts, both the chiral, pseudo‐ C 2 ‐symmetric diastereomer and the corresponding meso compound can be prepared. Cross double Mannich reactions of acetaldehyde with two different imines are also demonstrated.