An enantioselective process for the preparation of chiral...

Details An enantioselective process for the preparation of chiral... An enantioselective process for the preparation of chiral...

C - Chemistry, Metallurgy

07

D

C07D 417/06 (2006.01) C07D 213/24 (2006.01) C07D 213/30 (2006.01)

Patent

CA 2177817

An enantioselective multi-stage process is described which uses as a starting material an .alpha.,.beta.-unsaturated olefin of the formula (1): Ar- CH=C(R4)COAux, where Ar and R4, which may be the same or different, is each a monocyclic or bicyclic aryl group optionally containing one or more heteroatoms selected from oxygen, sulphur or nitrogen atoms; and Aux is the residue of a chiral (R- or S-) auxiliary. In the process, the olefin is converted to a chiral triarylethane which are useful as PDE IV inhibitors.

Dans ce procédé énantiosélectif en plusieurs étapes, on utilise en tant que matériau de départ une oléfine .alpha.,.beta.-insaturée possédant la formule (1) Ar-CH=C(R?4¿)COAux, dans laquelle Ar et R?4¿ qui peuvent être semblables ou différents représentent chacun un groupe aryle monocyclique ou bicyclique contenant facultativement un ou plusieurs hétéroatomes choisis parmi des atomes d'oxygène, de soufre ou d'azote; et Aux représente le résidu d'un auxiliaire (R- ou S-) chiral. Dans ce procédé, on convertit l'oléfine en triaryléthane chiral. Ces dérivés sont utiles en tant qu'inhibiteurs de la phosphodiestérase de type IV.

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