ortho-Diphenylphosphanylbenzoyl-dirigierte Hydroformylierung als Schlüsselschritt einer iterativen Polypropionatsynthese (English shop)

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Rhodium-catalysed hydroformylation offers an economically very attractive route for the introduction of the synthetically valuable aldehyde function under comparatively mild conditions. The chemo-, regio- and stereoselectivity can be controlled by a substrate-bound, catalyst-directing group; in this case the ortho-diphenylphosphanylbenzoyl group (o-DPPB).

This work presents a regio- and stereoselective hydroformylation of internal and terminal olefins that provides direct access to the anti-aldol retron.

Subsequent cuprate addition affords the corresponding secondary alcohol with good diastereoselectivity; this is followed by transesterification of the o-DPPB ester, which allows the preceding steps to be repeated. By means of this new method, polypropionate chains can be constructed in an iterative fashion.