Isothiourea-catalyzed enantioselective functionalization of 2-pyrrolyl acetic acid : two-step synthesis of stereodefined dihydroindolizinones
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).
Citation
Zhang , S , Taylor , J E , Slawin , A M Z & Smith , A D 2018 , ' Isothiourea-catalyzed enantioselective functionalization of 2-pyrrolyl acetic acid : two-step synthesis of stereodefined dihydroindolizinones ' , Organic Letters , vol. In press . https://doi.org/10.1021/acs.orglett.8b02423
Publication
Organic Letters
Status
Peer reviewed
ISSN
1523-7060Type
Journal article
Description
JET thanks The Leverhulme Trust for an Early Career Fellowship [ECF-2014-005]. ADS thanks the Royal Society for a Wolfson Research Merit Award.Collections
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