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Chiral magnesium BINOL phosphate-catalyzed phosphination of imines: access to enantioenriched ?-amino phosphine oxides.

ABSTRACT: A new method to synthesize chiral ?-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenylphosphine oxide nucleophiles also showed good reactivity.

SUBMITTER: Ingle GK 

PROVIDER: S-EPMC3115557 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Chiral magnesium BINOL phosphate-catalyzed phosphination of imines: access to enantioenriched α-amino phosphine oxides.

Ingle Gajendrasingh K GK   Liang Yuxue Y   Mormino Michael G MG   Li Guilong G   Fronczek Frank R FR   Antilla Jon C JC  

Organic letters 20110317 8

A new method to synthesize chiral α-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenyl  ...[more]

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