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

doi:10.1021/acs.orglett.8b02423

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

Department of Chemistry

University of St Andrews

Research output: Contribution to journal › Article › peer-review

25 Citations (SciVal)

128 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 language	English
Pages (from-to)	5482-5485
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	17
Early online date	24 Aug 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b02423
Publication status	Published - 7 Sept 2018

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b02423

Pyrrole CCl3_Org. Lett._Revised_Final
This document is the Accepted Manuscript of a Published Work that appeared in final form in Organic Letters, copyright (C) American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work, see: https://pubs.acs.org/doi/10.1021/acs.orglett.8b02423
Accepted author manuscript, 1.27 MB

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title = "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).",

author = "Shuyue Zhang and James Taylor and Slawin, \{Alexandra M.z.\} and Smith, \{Andrew D.\}",

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AU - Taylor, James

AU - Slawin, Alexandra M.z.

AU - Smith, Andrew D.

PY - 2018/9/7

Y1 - 2018/9/7

N2 - 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).

AB - 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).

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U2 - 10.1021/acs.orglett.8b02423

DO - 10.1021/acs.orglett.8b02423

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JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

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

Abstract

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