Diastereo- and Enantioselective Iridium Catalyzed Carbonyl (α-Cyclopropyl)allylation via Transfer Hydrogenation

Ryosuke Tsutsumi, Suckchang Hong, Michael J. Krische

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The first examples of diastereo- and enantioselective carbonyl α-(cyclopropyl)allylation are reported. Under the conditions of iridium catalyzed transfer hydrogenation using the chiral precatalyst (R)-Ir-I modified by SEGPHOS, carbonyl α-(cyclopropyl)allylation may be achieved with equal facility from alcohol or aldehyde oxidation levels. This methodology provides a conduit to hitherto inaccessible inaccessible enantiomerically enriched cyclopropane-containing architectures. Alcohol solves problems: Chiral iridium catalysts modified by (R)-SEGPHOS catalyze the transfer hydrogenative coupling of racemic α-cyclopropyl allyl acetate with diverse primary alcohols with good anti-diastereo- and exceptional enantioselectivity. These processes represent the first diastereo- and enantioselective carbonyl (α-cyclopropyl)allylations.

Original languageEnglish
Pages (from-to)12903-12907
Number of pages5
JournalChemistry - A European Journal
Volume21
Issue number37
DOIs
Publication statusPublished - 2015 Sep 1
Externally publishedYes

Keywords

  • cyclopropane
  • enantioselective catalysis
  • green chemistry
  • iridium
  • transfer hydrogenation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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