4.8 Article

Catalytic asymmetric Stetter reaction onto vinylphosphine oxides and vinylphosphonates

Journal

ORGANIC LETTERS
Volume 10, Issue 14, Pages 3141-3144

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol801047k

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Funding

  1. NIGMS NIH HHS [R01 GM072586-01A1, R01 GM072586, GM72586] Funding Source: Medline

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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 vinyl phosphonate Michael acceptor in yields up to 99% and ee values up to 96%.

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