Direct catalytic asymmetric intramolecular conjugate addition of thioamide to α,β-unsaturated esters

Yuta Suzuki, Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Proton transfer allows efficient access to optically active five- and six-membered ring systems bearing ester and thioamide functionalities in an anti fashion; these ring systems are amenable to differential functional group manipulation. Direct catalytic, asymmetric, intramolecular conjugate addition of thioamide to α,β-unsaturated esters is described. In situ generated Cu thioamide enolate, by catalytic deprotonation, underwent the conjugate addition/protonation, to achieve the complete transformation (see scheme).

Original languageEnglish
Pages (from-to)11998-12001
Number of pages4
JournalChemistry - A European Journal
Volume17
Issue number43
DOIs
Publication statusPublished - Oct 17 2011
Externally publishedYes

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Thioamides
Esters
Bearings (structural)
Deprotonation
Proton transfer
Protonation
Functional groups

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Direct catalytic asymmetric intramolecular conjugate addition of thioamide to α,β-unsaturated esters. / Suzuki, Yuta; Yazaki, Ryo; Kumagai, Naoya; Shibasaki, Masakatsu.

In: Chemistry - A European Journal, Vol. 17, No. 43, 17.10.2011, p. 11998-12001.

Research output: Contribution to journalArticle

Suzuki, Yuta ; Yazaki, Ryo ; Kumagai, Naoya ; Shibasaki, Masakatsu. / Direct catalytic asymmetric intramolecular conjugate addition of thioamide to α,β-unsaturated esters. In: Chemistry - A European Journal. 2011 ; Vol. 17, No. 43. pp. 11998-12001.
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