Isothiourea-Catalyzed Enantioselective Functionalization of 2-Pyrrolyl Acetic Acid: Two-Step Synthesis of Stereodefined Dihydroindolizinones

Shuyue Zhang, James Taylor, Alexandra M.z. Slawin, Andrew D. Smith

Research output: Contribution to journalArticle

6 Citations (Scopus)
14 Downloads (Pure)

Abstract

Catalytic enantioselective functionalization of 2-pyrrolyl acetic acid with trichloromethyl enones using isothiourea catalysis is reported, leading to a range of stereodefined diesters and diamides after nucleophilic ring opening with either methanol or benzylamine (30 examples, up to >95:5 dr and >99:1 er). Subsequent intramolecular Friedel–Crafts reaction allows access to dihydroindolizinones in high yields and stereofidelity (6 examples, up to >95:5 dr and 99:1 er).
Original languageEnglish
Pages (from-to)5482-5485
Number of pages4
JournalOrganic Letters
Volume20
Issue number17
Early online date24 Aug 2018
DOIs
Publication statusPublished - 7 Sep 2018

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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