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Synlett 2012; 23(19): 2817-2821
DOI: 10.1055/s-0032-1317512
DOI: 10.1055/s-0032-1317512
letter
Asymmetric Rhodium-Catalysed Addition of Arylboronic Acids to Acyclic Unsaturated Esters Containing a Basic γ-Amino Group
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.
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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].