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

doi:10.1021/acs.orglett.8b02423

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 journal › Article › peer-review

20 Citations (Scopus)

4 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
Journal	Organic Letters
Volume	In press
Early online date	24 Aug 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b02423
Publication status	E-pub ahead of print - 24 Aug 2018

Access to Document

10.1021/acs.orglett.8b02423

Smith_2018_OL_IsoPyrrole_AAM
Copyright © 2018 American Chemical Society. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1021/acs.orglett.8b02423
Accepted author manuscript, 1.16 MB

Cite this

@article{895e5f32169147cba00d70a13b8de9ba,

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 Taylor, {James Edward} and Slawin, {Alexandra M. Z.} and Smith, {Andrew D.}",

note = "JET thanks The Leverhulme Trust for an Early Career Fellowship [ECF-2014-005]. ADS thanks the Royal Society for a Wolfson Research Merit Award.",

year = "2018",

month = aug,

day = "24",

doi = "10.1021/acs.orglett.8b02423",

language = "English",

volume = "In press",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

}

TY - JOUR

T1 - Isothiourea-catalyzed enantioselective functionalization of 2-pyrrolyl acetic acid

T2 - two-step synthesis of stereodefined dihydroindolizinones

AU - Zhang, Shuyue

AU - Taylor, James Edward

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

N1 - JET thanks The Leverhulme Trust for an Early Career Fellowship [ECF-2014-005]. ADS thanks the Royal Society for a Wolfson Research Merit Award.

PY - 2018/8/24

Y1 - 2018/8/24

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).

UR - https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.8b02423

U2 - 10.1021/acs.orglett.8b02423

DO - 10.1021/acs.orglett.8b02423

M3 - Article

SN - 1523-7060

VL - In press

JO - Organic Letters

JF - Organic Letters

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Catalytic Activation: Catalytic Activation of Carboxylic Acids and Alcohols

RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications