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1999•Organic LettersOpen access

A Novel Resolution Procedure for the Preparation of P-Stereogenic Phosphine Oxides

Neil G. Andersen, Philip Ramsden, Daqing Che, Masood Parvez, Brian A. Keay

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Abstract

A new general route for preparing enantiomerically pure P-stereogenic phosphine oxides has been developed by exploiting the Staudinger reaction between racemic tertiary phosphines and an enantiomerically pure organoazide. The resulting phosphinimines are easily resolved by either crystallization or flash chromatography and serve as synthetic intermediates toward enantiomerically pure phosphine oxides.

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A new general route for preparing enantiomerically pure P-stereogenic phosphine oxides has been developed by exploiting the Staudinger reaction between racemic tertiary phosphines and an enantiomerically pure organoazide. The resulting phosphinimines are easily resolved by either crystallization or flash chromatography and serve as synthetic intermediates toward enantiomerically pure phosphine oxides.

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Available abstract

A new general route for preparing enantiomerically pure P-stereogenic phosphine oxides has been developed by exploiting the Staudinger reaction between racemic tertiary phosphines and an enantiomerically pure organoazide. The resulting phosphinimines are easily resolved by either crystallization or flash chromatography and serve as synthetic intermediates toward enantiomerically pure phosphine oxides.

Key concepts: Stereocenter, Phosphine, Chemistry, Resolution (logic), Crystallization, Combinatorial chemistry, Organic chemistry, Enantioselective synthesis

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