Asymmetric Rhodium-Catalysed Addition of Arylboronic Acids to Acyclic 
Unsaturated Esters Containing a Basic γ-Amino Group

Niall A. Anderson; Brendan J. Fallon; Elena Valverde; Simon J. F. MacDonald; John M. Pritchard; Colin J. Suckling; Allan J. B. Watson

doi:10.1055/s-0032-1317512

Synlett, Table of Contents

Synlett 2012; 23(19): 2817-2821
DOI: 10.1055/s-0032-1317512

letter

Asymmetric Rhodium-Catalysed Addition of Arylboronic Acids to Acyclic Unsaturated Esters Containing a Basic γ-Amino Group

Niall A. Anderson*

^aDepartment of Medicinal Chemistry, Fibrosis DPU, Respiratory CEDD, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK Fax: +44(1438)768302 Email: niall.a.anderson@gsk.com

,

Brendan J. Fallon

^aDepartment of Medicinal Chemistry, Fibrosis DPU, Respiratory CEDD, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK Fax: +44(1438)768302 Email: niall.a.anderson@gsk.com

,

Elena Valverde

^aDepartment of Medicinal Chemistry, Fibrosis DPU, Respiratory CEDD, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK Fax: +44(1438)768302 Email: niall.a.anderson@gsk.com

,

Simon J. F. MacDonald

^aDepartment of Medicinal Chemistry, Fibrosis DPU, Respiratory CEDD, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK Fax: +44(1438)768302 Email: niall.a.anderson@gsk.com

,

John M. Pritchard

^aDepartment of Medicinal Chemistry, Fibrosis DPU, Respiratory CEDD, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK Fax: +44(1438)768302 Email: niall.a.anderson@gsk.com

,

Colin J. Suckling

^bWestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK

,

Allan J. B. Watson

^bWestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK

› Author Affiliations

Abstract

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Abstract

Application of the Miyaura–Hayashi rhodium-catalysed addition of aryl boronic acids to acyclic unsaturated esters featuring basic centres to yield γ-amino butyric acids incorporating a substituted β-phenyl group is described. Unoptimised isolated yields and enantiomeric excesses vary from moderate to excellent, and the method tolerates a variety of substitution patterns and a range of functionality.

Key words

rhodium - asymmetric 1,4-addition - drugs - γ-aminobutyric acid - synthesis

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References

References and Notes
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