Direct catalytic aldol-type reactions using RCH2CN

Yutaka Suto, Naoya Kumagai, Shigeki Matsunaga, Motomu Kanai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

128 Citations (Scopus)


(Matrix presented) A copper fluoride-catalyzed cyanomethylation that can be applied to a wide range of ketones and aldehydes was developed using TMSCH2CN as a nucleophile. The reaction was extended to a conceptually more advanced copper alkoxide-catalyzed direct addition of alkylnitriles to aldehydes, which can act as a surrogate direct catalytic aldol reaction of esters. These reactions can be applied to the first catalytic enantioselective cyanomethylation of ketones and direct catalytic enantioselective cyanomethylation of aldehydes.

Original languageEnglish
Pages (from-to)3147-3150
Number of pages4
JournalOrganic Letters
Issue number17
Publication statusPublished - 2003 Aug 21
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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