Enantioselective Formal C(sp2)−H Vinylation

Madhu Sudan Manna, Rahul Sarkar, Santanu Mukherjee

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

An enantioselective formal C(sp2)−H vinylation of prochiral 2,2-disubstituted cyclopentene-1,3-dione is presented. This vinylative desymmetrization is realized by using a two-step procedure that consists of a catalytic enantioselective vinylogous Michael addition of deconjugated butenolides to cyclopentene-1,3-dione and a base-mediated decarboxylation. The overall process utilizes deconjugated butenolides as the source of the highly substituted vinyl unit. Five-membered carbocycles containing a remote all-carbon quaternary stereogenic center are obtained in good yields and with good to high enantioselectivities.

Original languageEnglish (US)
Pages (from-to)14912-14919
Number of pages8
JournalChemistry - A European Journal
Volume22
Issue number42
DOIs
StatePublished - Oct 10 2016
Externally publishedYes

Keywords

  • C−H functionalization
  • decarboxylation
  • desymmetrization
  • lactones
  • vinylation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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