Evidence for an enolate mechanism in the asymmetric Michael reaction of α,β-unsaturated aldehydes and ketones: Via a hybrid system of two secondary amine catalysts

Nariyoshi Umekubo, Takahiro Terunuma, Eunsang Kwon, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

The key nucleophile was found to be neither an enamine nor an enol, but an enolate in the direct Michael reaction of α,β-unsaturated aldehydes and non-activated ketones catalyzed by two amine catalysts namely diphenylprolinol silyl ether and pyrrolidine. This is a rare example of an enolate from a ketone serving as a key intermediate in the asymmetric organocatalytic reaction involving secondary amine catalysts because the ketone enolates are generally generated using a strong base, and the enamine is a common nucleophile in this type of reaction. This journal is

Original languageEnglish
Pages (from-to)11293-11297
Number of pages5
JournalChemical Science
Volume11
Issue number41
DOIs
Publication statusPublished - 2020 Nov 7

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Evidence for an enolate mechanism in the asymmetric Michael reaction of α,β-unsaturated aldehydes and ketones: Via a hybrid system of two secondary amine catalysts'. Together they form a unique fingerprint.

Cite this