Catalytic asymmetric direct vinylogous michael addition of deconjugated butenolides to maleimides for the construction of quaternary stereogenic centers

Madhu Sudan Manna, Santanu Mukherjee

Research output: Contribution to journalArticlepeer-review

68 Scopus citations

Abstract

Competition under control: A practical and efficient direct asymmetric vinylogous Michael reaction of deconjugated butenolides has been developed (see scheme). The products of this reaction, highly functionalized chiral succinimides, are obtained in excellent yield with high diastereoselectivity (up to d.r.=18:1) and outstanding enantioselectivity (up to e.r.=99.5:0.5).

Original languageEnglish (US)
Pages (from-to)15277-15282
Number of pages6
JournalChemistry - A European Journal
Volume18
Issue number48
DOIs
StatePublished - Nov 26 2012
Externally publishedYes

Keywords

  • asymmetric catalysis
  • butyrolactone
  • maleimide
  • Michael addition
  • thiourea

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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