Chemistry - A European Journal p. 4044 - 4048 (2009)
Update date:2022-09-26
Topics:
Dziedzic, Pawel
Schyman, Patrie
Kullberg, Martin
Cordova, Armando
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 α-hydroxy-β- benzoylami-noaldehydes (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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