A General Organocatalytic System for Enantioselective Radical Conjugate Additions to Enals

Emilien Le Saux, Dengke Ma, Pablo Bonilla, Catherine M. Holden, Danilo Lustosa, Paolo Melchiorre

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

Abstract

Herein, we report a general iminium ion-based catalytic method for the enantioselective conjugate addition of carbon-centered radicals to aliphatic and aromatic enals. The process uses an organic photoredox catalyst, which absorbs blue light to generate radicals from stable precursors, in combination with a chiral amine catalyst, which secures a consistently high level of stereoselectivity. The generality of this catalytic platform is demonstrated by the stereoselective interception of a wide variety of radicals, including non-stabilized primary ones which are generally difficult to engage in asymmetric processes. The system also served to develop organocatalytic cascade reactions that combine an iminium-ion-based radical trap with an enamine-mediated step, affording stereochemically dense chiral products in one-step.

Original languageEnglish
Pages (from-to)5357-5362
Number of pages6
JournalAngewandte Chemie - International Edition
Volume60
Issue number10
DOIs
StatePublished - 1 Mar 2021
Externally publishedYes

Keywords

  • asymmetric catalysis
  • cascade reactions
  • organocatalysis
  • photoredox catalysis
  • radical chemistry

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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