Organic Letters, volume 6, issue 18, pages 3055-3058

Enantioselective Partial Reduction of 2,5-Disubstituted Pyrroles via a Chiral Protonation Approach

Timothy J Donohoe ¹

Graeme C Freestone ¹

Catherine E Headley ¹

Caroline L Rigby ¹

Rick P.C Cousins ¹

Gurdip Bhalay ¹

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK, GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage SG1 2NY, UK, and Novartis Horsham Research Centre, Wimblehurst Road, Horsham, West Sussex RH12 5AB, UK

Publication type: Journal Article

Publication date: 2004-07-31

American Chemical Society (ACS)

Journal: Organic Letters

scimago Q1

wos Q1

SJR: 1.245

CiteScore: 9.3

Impact factor: 4.9

ISSN: 15237060, 15237052

DOI: 10.1021/ol049014q

Copy DOI

PubMed ID: 15330586

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

[reaction: see text] The partial reduction of 2,5-pyrrole diester 1 followed by enantioselective protonation in situ to furnish synthetically useful building blocks is described. An enantiomeric excess of up to 74% was achieved using (-)-ephedrine and related analogues as chiral proton sources. The pyrroline product obtained could be recrystallized to give enantiomerically pure material.

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Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.245

CiteScore

9.3

Impact factor

4.9

ISSN

15237060 (Print)

15237052 (Electronic)

Enantioselective Partial Reduction of 2,5-Disubstituted Pyrroles via a Chiral Protonation Approach

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