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Synthesis of P-Stereogenic Centers Through Ring-Closing Metathesis

James Harvey, Steven J. Malcolmson, Katherine S. Dunne, Simon J. Meek, A. L. Thompson, Richard R. Schrock, Amir H. Hoveyda, Véronique Gouverneur

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Abstract

Significance Chiral phosphinates and phosphine oxides are an important class of molecules owing to their abundant use as ligands and Lewis base catalysts. Asymmetric synthesis of these motifs, however, is not trivial and the authors report a new approach towards these targets. Through asymmetric ring-closing metathesis, phosphinates ( 5 ) and phosphine oxides ( 7 ) bearing P-stereogenic centers are obtained in moderate yields and selectivity.

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What this paper is about

Significance Chiral phosphinates and phosphine oxides are an important class of molecules owing to their abundant use as ligands and Lewis base catalysts. Asymmetric synthesis of these motifs, however, is not trivial and the authors report a new approach towards these targets. Through asymmetric ring-closing metathesis, phosphinates ( 5 ) and phosphine oxides ( 7 ) bearing P-stereogenic centers are obtained in moderate yields and selectivity.

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Available abstract

Significance Chiral phosphinates and phosphine oxides are an important class of molecules owing to their abundant use as ligands and Lewis base catalysts. Asymmetric synthesis of these motifs, however, is not trivial and the authors report a new approach towards these targets. Through asymmetric ring-closing metathesis, phosphinates ( 5 ) and phosphine oxides ( 7 ) bearing P-stereogenic centers are obtained in moderate yields and selectivity.

Key concepts: Stereocenter, Chemistry, Ring-closing metathesis, Metathesis, Phosphine, Lewis acids and bases, Stereochemistry, Ring (chemistry)

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