4.8 Article

Catalytic Asymmetric Conjugate Addition of α-Cyanoketones for the Construction of a Quaternary Stereogenic Center

Journal

ORGANIC LETTERS
Volume 12, Issue 7, Pages 1484-1487

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol100183s

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Funding

  1. JSPS

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The catalytic asymmetric conjugate addition of alpha-cyanoketone pronucleophiles to vinyl ketones promoted by a Y/1 catalyst is described. High enantioselectivity was observed for a range of aromatic vinyl ketones, providing 1,5-dicarbonyl compounds bearing an all-carbon quaternary stereogenic center. The product was successfully converted to a spiro-piperidine entity and a bicyclo[3.3.0]octane framework through either the reduction of nitrile or intramolecular pinacol coupling.

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