Synlett 2012; 23(19): 2817-2821
DOI: 10.1055/s-0032-1317512
letter
© Georg Thieme Verlag Stuttgart · New York

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

Authors

  • Niall A. Anderson*

    a   Department 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

    a   Department 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

    a   Department 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

    a   Department 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

    a   Department 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

    b   WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK
  • Allan J. B. Watson

    b   WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK
Further Information

Publication History

Received: 30 August 2012

Accepted after revision: 05 October 2012

Publication Date:
31 October 2012 (online)


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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.