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: 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
› 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

  • 1 Li K, Xu E. Neurosci. Bull. 2008; 24: 195
  • 2 Gajcyl K, Lochy S, Librowski T. Curr. Med. Chem. 2010; 17: 2338
  • 3 Brock S, Hose DR. J, Moseley JD, Parker AJ, Patel I, Williams AJ. Org. Process Res. Dev. 2008; 12: 496
  • 4 Belyk KM, Beguin CD, Palucki M, Grinberg N, DaSilva J, Askin D, Yasuda N. Tetrahedron Lett. 2004; 45: 3265
  • 5 Collier PN. Tetrahedron Lett. 2009; 50: 3909
  • 6 Tsakai M, Hayashi H, Miyaura N. Organometallics 1997; 16: 4429
  • 7 Tian P, Dong HQ, Lin GQ. ACS Catal. 2012; 2: 95
  • 8 Takaya Y, Ogasawara M, Hayashi T, Miyaura N. J. Am. Chem. Soc. 1998; 120: 5579
  • 9 Shen B, Johnston JN. Org. Lett. 2008; 10: 4397
  • 10 Meyer O, Becht JM, Helmchen G. Synlett 2003; 1539
  • 11 Takaya Y, Senda T, Kurushima H, Ogasawara M, Hayashi T. Tetrahedron: Asymmetry 1999; 10: 4047
  • 12 Chiralpak AD-H, column 4.6 mm id × 25 cm, heptane–EtOH (85:15; +0.2% isopropylamine), flow rate = 1.0 mL/min, isomer 1 elutes ca. 21 min, isomer 2 elutes ca. 30 min.
  • 13 Shintani R, Ueyama K, Yamada I, Hayashi T. Org. Lett. 2004; 6: 3425
  • 14 Crystallographic data (excluding structural factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC897927. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, [fax: +44(1223)336033 or e-mail: deposit@CCDC.cam.ac.uk].