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Organocatalytic enantioselective synthesis of both diastereomers of alpha-hydroxyphosphinates.

ABSTRACT: Racemic alpha-acylphosphinates and formylphosphinate hydrate were used directly as the substrates in a proline derivative-catalyzed cross aldol reaction with ketones. Because of the preexisting phosphorus stereogenic center, a mixture of two diastereomers of the corresponding alpha-hydroxyphosphinates was obtained in this reaction. Good to high enantioselectivities (up to 99% ee) were obtained simultaneously for the two diastereomers in good yields. Good diastereoselectivities were also obtained when the reaction generates an additional carbon stereogenic center.

SUBMITTER: Samanta S

PROVIDER: S-EPMC2821456 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Organocatalytic enantioselective synthesis of both diastereomers of alpha-hydroxyphosphinates.

Samanta Sampak S Perera Sandun S Zhao Cong-Gui CG

The Journal of organic chemistry 20100201 4

Racemic alpha-acylphosphinates and formylphosphinate hydrate were used directly as the substrates in a proline derivative-catalyzed cross aldol reaction with ketones. Because of the preexisting phosphorus stereogenic center, a mixture of two diastereomers of the corresponding alpha-hydroxyphosphinates was obtained in this reaction. Good to high enantioselectivities (up to 99% ee) were obtained simultaneously for the two diastereomers in good yields. Good diastereoselectivities were also obtained ...[more]

PMID: 20085234

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