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Catalytic asymmetric stetter reaction onto vinylphosphine oxides and vinylphosphonates.

ABSTRACT: An intramolecular Stetter reaction of vinylphosphine oxides and vinylphosphonates has been developed. Treatment of an aldehyde with a nucleophilic N-heterocyclic carbene catalyst allows for addition of an acyl anion equivalent into a vinylphosphine oxide or vinylphosphonate Michael acceptor in yields up to 99% and ee values up to 96%.

SUBMITTER: Cullen SC 

PROVIDER: S-EPMC2746454 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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Catalytic asymmetric stetter reaction onto vinylphosphine oxides and vinylphosphonates.

Cullen Steven C SC   Rovis Tomislav T  

Organic letters 20080613 14

An intramolecular Stetter reaction of vinylphosphine oxides and vinylphosphonates has been developed. Treatment of an aldehyde with a nucleophilic N-heterocyclic carbene catalyst allows for addition of an acyl anion equivalent into a vinylphosphine oxide or vinylphosphonate Michael acceptor in yields up to 99% and ee values up to 96%. ...[more]

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