Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes

Eric R. Welin, Alexander A. Warkentin, Jay C. Conrad, David W.C. MacMillan

Research output: Contribution to journalArticle

76 Scopus citations

Abstract

The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α-cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (-)-bursehernin. A combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective cyanoalkylation of aldehydes. This synergistic catalysis protocol makes possible the coupling of two highly versatile yet orthogonal functionalities.

Original languageEnglish (US)
Pages (from-to)9668-9672
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number33
DOIs
StatePublished - Aug 1 2015

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • aldehydes
  • alkylation
  • organocatalysis
  • photoredox catalysis
  • total synthesis

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