Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 16, Pages 4044-4048Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900078
Keywords
aldehydes; asymmetric catalysis; (phenylmethylene)benzamides; organocatalysis; taxol
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A simple highly enantioselective organocatalytic addition of aldehydes to N-(phenylmethylene)benzamides is presented. The application of (R)-proline as the catalyst and subsequent oxidation of the protected alpha-hydroxy-beta-benzoylaminoaldehydes (92%-99% ee) gives access to esterification-ready phenylisoserine derivatives such as the protected paclitaxel (taxol) side chain. Esterification of these derivatives with baccatin III gives access to the cancer chemotherapeutic substance paclitaxel and its analogues that do not exist in nature.
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