Catalytic asymmetric conjugate addition of α-cyanoketones for the construction of a quaternary stereogenic center

Yuji Kawato, Noriko Takahashi, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

38 Citations (Scopus)

Abstract

(Figure Presented) The catalytic asymmetric conjugate addition of a-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.

Original languageEnglish
Pages (from-to)1484-1487
Number of pages4
JournalOrganic Letters
Volume12
Issue number7
DOIs
Publication statusPublished - 2010 Apr 2
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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