A strategy enabling enantioselective direct conjugate addition of inert aryl methane nucleophiles to enals with a chiral amine catalyst under mild conditions

Tengfei Li, Jin Zhu, Deyan Wu, Xiangmin Li, Sinan Wang, Hao Li, Jian Li, Wei Wang

Research output: Contribution to journalArticlepeer-review

64 Scopus citations

Abstract

Nitro-charged activation: An organocatalytic enantioselective conjugate addition of aryl methyl nucleophiles to enals has been developed to produce ubiquitous chiral benzylic building blocks (see scheme; TES=triethylsilyl). Taking advantage of the strongly electron-withdrawing nature of nitro groups, which can be conveniently transformed into other functionalities, this functionality was incorporated into aromatic systems as a temporary activating group.

Original languageEnglish (US)
Pages (from-to)9147-9150
Number of pages4
JournalChemistry - A European Journal
Volume19
Issue number28
DOIs
StatePublished - Jul 8 2013
Externally publishedYes

Keywords

  • aryl methane
  • enals
  • iminium catalysis
  • Michael addition
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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