Isothiourea-catalyzed enantioselective functionalization of 2-pyrrolyl acetic acid: two-step synthesis of stereodefined dihydroindolizinones

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

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

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
JournalOrganic Letters
VolumeIn press
Early online date24 Aug 2018
DOIs
Publication statusE-pub ahead of print - 24 Aug 2018

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