Volume 28, Issue 50
Preparative Organic Chemistry
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ChemInform Abstract: Substrate-Directed Diastereoselective Hydroformylation. Part 1. Substrate-Directed Diastereoselective Hydroformylation of Methallylic Alcohols - Development of an Efficient Catalyst-Directing Group for Rhodium-Catalyzed Hydroformylation.

B. BREIT

B. BREIT

Fachbereich Chem., Philipps-Univ., D-35043 Marburg, Germany

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First published: 02 August 2010

Abstract

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ChemInform Abstract

The protection of methallylic alcohols (I) with the o-( diphenylphosphanyl)benzoyl group (Dpb) leads to the development of an optimized, substrate-directed, highly diastereoselective, rhodium- catalyzed hydroformylation method, which provides stereoselective access to acyclic building blocks of type (V) containing two adjacent stereocenters. Subsequent transformation to the corresponding γ- lactones, e.g. (VI), is readily achieved without loss of stereoselectivity.

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