Highly Enantio- And Diastereoselective Synthesis of 1,2,3-Trisubstituted Cyclopropanes from α,β-Unsaturated Amides and Stabilized Sulfur Ylides Catalyzed by a Chiral Copper(I) Complex

Santosh K. Pagire, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The stereoselective preparation of 1,2,3-substituted cyclopropanes from α,β-unsaturated carbonyl compounds in the carboxylic acid oxidation state through Michael addition-initiated ring-closure reactions is a significant challenge in organic synthesis. Herein, the previously elusive catalytic asymmetric cyclopropanation of α,β-unsaturated amides with stabilized sulfur ylides has been efficiently accomplished utilizing a chiral Cu(I) complex. This Lewis acid catalytic system effectively converts a wide range of electron-deficient alkenes into the corresponding 1,2,3-trisubstituted cyclopropanes under mild reaction conditions in good to excellent yields with both high to excellent enantio- and diastereoselectivities. The resulting enantiomerically enriched cyclopropane amides can be readily diversified into promising synthetic intermediates such as β-aminocyclopropanecarboxylic acids with the facile recovery of the 7-azaindoline auxiliary without influencing the optical purity of the cyclopropane unit, which highlights the synthetic efficacy of this catalytic approach.

Original languageEnglish
Pages (from-to)11597-11606
Number of pages10
JournalACS Catalysis
DOIs
Publication statusAccepted/In press - 2021

Keywords

  • 7-azaindolines
  • asymmetric synthesis
  • Cu catalysis
  • cyclopropanes
  • ligand
  • sulfur ylides

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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