Organocatalytic asymmetric Mannich reactions of 5H-oxazol-4-ones : highly enantio- and diastereoselective synthesis of chiral α-alkylisoserine derivatives
Date of Issue2013
School of Physical and Mathematical Sciences
The first organocatalytic Mannich reaction of 5H-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.
Advanced synthesis & catalysis
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