4.3 Article

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

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PURE AND APPLIED CHEMISTRY
卷 88, 期 4, 页码 333-339

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WALTER DE GRUYTER GMBH
DOI: 10.1515/pac-2016-0103

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boranes; chirality; ESOC-19; mechanism; phosphorus chemistry

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We present recent advances in the understanding of the reduction of optically pure hydroxy-alkylphosphinates 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 center dot THF, which plays three roles: activating, reducing and protecting agent. The formation of by-products as hydroxyalkyl secondary phosphine-boranes has also been studied.

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