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Diametric stereocontrol in dynamic catalytic reduction of racemic acyl phosphonates: divergence from ?-keto ester congeners.

ABSTRACT: An unexpected dichotomy was observed in the Ru-catalyzed asymmetric transfer hydrogenation of acyl phosphonates: reduction proceeded from the opposite face relative to that observed in the analogous reduction of ?-keto esters. The first highly selective catalytic hydrogenation of acyl phosphonates was utilized in the dynamic kinetic resolution of ?-aryl acyl phosphonates, providing ?-stereogenic ?-hydroxy phosphonic acid derivatives.

SUBMITTER: Corbett MT

PROVIDER: S-EPMC3552383 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Diametric stereocontrol in dynamic catalytic reduction of racemic acyl phosphonates: divergence from α-keto ester congeners.

Corbett Michael T MT Corbett Michael T MT Johnson Jeffrey S JS

Journal of the American Chemical Society 20130108 2

An unexpected dichotomy was observed in the Ru-catalyzed asymmetric transfer hydrogenation of acyl phosphonates: reduction proceeded from the opposite face relative to that observed in the analogous reduction of α-keto esters. The first highly selective catalytic hydrogenation of acyl phosphonates was utilized in the dynamic kinetic resolution of α-aryl acyl phosphonates, providing β-stereogenic α-hydroxy phosphonic acid derivatives. ...[more]

PMID: 23297694

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