PaaSicats: Powerful catalysts for asymmetric epoxidation of enones. Novel syntheses of α-arylpropanoic acids including (S)-fenoprofen

DOI: 10.1016/S0040-4039(99)01022-9

Source and publish data:

Tetrahedron Letters p. 5421 - 5424 (1999)

Update date:2022-08-03

Topics:

Authors:

Carde, Lydia

Davies, Huw

Geller, Thomas P.

Roberts, Stanley M.

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Article abstract of DOI:10.1016/S0040-4039(99)01022-9

Application of the recently developed silica-adsorbed polyleucine catalysts to the enantioselective epoxidation of two enones is reported. Treatment of these epoxides with trimethylaluminium in moist dichloromethane generates the α-hydroxy-β-methylketones, with inversion of configuration. Diastereoselective reduction of the ketone moiety followed by oxidative cleavage generates α-arylpropanoic acids.

Full text of DOI:10.1016/S0040-4039(99)01022-9

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