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

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: [email protected]
,
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: [email protected]
,
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: [email protected]
,
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: [email protected]
,
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: [email protected]
,
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
› Author Affiliations
Further Information

Publication History

Received: 30 August 2012

Accepted after revision: 05 October 2012

Publication Date:
31 October 2012 (online)


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.

 
  • References and Notes

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