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Proline‐Catalyzed Mannich Reaction of Aldehydes with N ‐Boc‐Imines
Author(s) -
Yang Jung Woon,
Stadler Michael,
List Benjamin
Publication year - 2007
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.200603188
Subject(s) - mannich reaction , proline , chemistry , catalysis , amino acid , organic chemistry , aldimine , reaction conditions , medicinal chemistry , biochemistry
A curious cat. : The proline‐catalyzed Mannich reaction between aldehydes and N ‐Boc‐imines (Boc= tert ‐butoxycarbonyl) gives crystalline β‐amino aldehydes with exceptionally high diastereoselectivities and enantioselectivities (see scheme). The products of this reaction typically precipitate from the reaction mixture and are useful intermediates in the synthesis of α‐ and β‐substituted β‐amino acids.