Mechanistic aspects of the stereospecific reduction of chiral hydroxyalkyl phosphinates and phosphine oxides

Author:

Lemouzy Sébastien1,Nguyen Duc Hanh1,Gatineau David1,Giordano Laurent1,Hérault Damien1,Buono Gérard1

Affiliation:

1. 1Aix Marseille Université, Centrale Marseille, CNRS iSm2 UMR 7313, 13397, Marseille, France

Abstract

AbstractWe present recent advances in the understanding of the reduction of optically pure hydroxyalkylphosphinates and phosphine oxides, which represent key intermediates for the preparation of P-stereogenic ligands. Their reduction leads to P-chiral phosphinites and phosphines, respectively, and occurs stereospecifically with inversion of configuration using BH3·THF, which plays three roles: activating, reducing and protecting agent. The formation of by-products as hydroxyalkyl secondary phosphine–boranes has also been studied.

Publisher

Walter de Gruyter GmbH

Subject

General Chemical Engineering,General Chemistry

Reference64 articles.

1. The Hydroxyalkyl Moiety As a Protecting Group for the Stereospecific Alkylation of Masked Secondary Phosphine-Boranes

2. A General Strategy for the Synthesis of P-Stereogenic Compounds

3. H-Adamantylphosphinates as Universal Precursors of P-Stereogenic Compounds

4. Characterization of RP To the solution of SP g in freshly distilled THF mL ) was slowly added the solution of BH in THF equiv at and under stirring conditions The reaction mixture was allowed to warm at room temperature for The NMR analysis shown a mixture,1972

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