Enantioselective Diels-Alder reaction of α-(acylthio)acroleins: A new entry to sulfur-containing chiral quaternary carbons

Akira Sakakura, Hiroki Yamada, Kazuaki Ishihara

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A catalytic and enantioselective Diels-Alder reaction of α-(carbamoylthio)acroleins induced by an organoammonium salt of chiral triamine is described. α-(Carbamoylthio)acroleins are designed and synthesized as new sulfur-containing dienophiles for the first time. The Diels-Alder reaction affords chiral tertiary thiol precursors with up to 91% ee.

Original languageEnglish
Pages (from-to)2972-2975
Number of pages4
JournalOrganic Letters
Volume14
Issue number12
DOIs
Publication statusPublished - Jun 15 2012
Externally publishedYes

Fingerprint

acroleins
Diels-Alder reactions
Cycloaddition Reaction
Sulfur
Sulfhydryl Compounds
entry
sulfur
Carbon
Salts
carbon
thiols
salts

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Enantioselective Diels-Alder reaction of α-(acylthio)acroleins : A new entry to sulfur-containing chiral quaternary carbons. / Sakakura, Akira; Yamada, Hiroki; Ishihara, Kazuaki.

In: Organic Letters, Vol. 14, No. 12, 15.06.2012, p. 2972-2975.

Research output: Contribution to journalArticle

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