Chemoselective catalytic conjugate addition of alcohols over amines

Shuhei Uesugi, Zhao Li, Ryo Yazaki, Takashi Ohshima

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

A highly chemoselective conjugate addition of alcohols in the presence of amines is described. The cooperative nature of the catalyst enabled chemoselective activation of alcohols over amines, allowing the conjugate addition to soft Lewis basic α,β-unsaturated nitriles. Divergent transformation of the nitrile functionality highlights the utility of the present catalysis. The cooperative nature of a copper catalyst enabled the highly chemoselective activation of alcohols in the presence of amines and thus the conjugate addition of the hydroxy group to soft Lewis basic α,β-unsaturated nitriles. The presented method proceeds under proton-transfer conditions, reverses the innate reactivity of the OH and NH groups, and does not require protecting groups. dppe=1,2-bis(diphenylphosphino) ethane, MeSal=3-methylsalicylate.

Original languageEnglish
Pages (from-to)1611-1615
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number6
DOIs
Publication statusPublished - Feb 3 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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