Premium
Organocatalytic Asymmetric Mannich Reactions of 5 H ‐Oxazol‐4‐ones: Highly Enantio‐ and Diastereoselective Synthesis of Chiral α‐Alkylisoserine Derivatives
Author(s) -
Han Zhiqiang,
Yang Wenguo,
Tan ChoonHong,
Jiang Zhiyong
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300135
Subject(s) - chemistry , mannich reaction , cinchona , enantiomer , adduct , organocatalysis , catalysis , organic chemistry , amine gas treating , aryl , enantioselective synthesis , combinatorial chemistry , alkyl
The first organocatalytic Mannich reaction of 5 H ‐oxazol‐4‐ones with various readily prepared aryl‐ and alkylsulfonimides has been developed. Two commercially available pseudoenantiomeric Cinchona alkaloids‐derived tertiary amine/ureas have been demonstrated as the most efficient catalysts to access the opposite enantiomers of the Mannich products with equally excellent enantio‐ and diastereoselectivities. From the Mannich adducts, important α‐methyl‐α‐hydroxy‐β‐amino acid derivatives, such as the α‐methylated C‐13 side chain of taxol and taxotere, can be conveniently prepared.