CuI-catalyzed coupling reaction of β-amino acids or esters with aryl halides at temperature lower than that employed in the normal Ullmann reaction. Facile synthesis of SB-214857

Organic Letters

Volumn 3, Issue 16, 2001, Pages 2583-2586

  Ma, Dawei ^a   Xia, Chengfeng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BENZODIAZEPINE DERIVATIVE; COPPER; FIBRINOGEN RECEPTOR; HALOGENATED HYDROCARBON; LOTRAFIBAN; PIPERIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; BENZODIAZEPINES; CATALYSIS; COPPER; HYDROCARBONS, HALOGENATED; PIPERIDINES; PLATELET GLYCOPROTEIN GPIIB-IIIA COMPLEX; STEREOISOMERISM;

EID: 0035833707     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016258r     Document Type: Article

References (12)

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2. Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
3. (a) Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry, 1991, 2, 183.
4. (b) Davies, S. G.; Ichihara, O.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1141.
5. Typical Procedure. To a solution of aryl halide (1 mmol) and β-amino ester (1 mmol) in 5 mL of DMF were added potassium carbonate (2.5 mmol), 0.1 mL of water, and CuI (0.1 mmol) under nitrogen. After the mixture was stirred at 100 °C for 48 h under nitrogen atmosphere, the cooled solution was concentrated in vacuo. The residue was dissolved in water, acidified to pH 5, and extracted with ethyl acetate. The combined organic layers were concentrated and purified by chromatography to afford the corresponding N-aryl β-amino acid.
6. Greenstein, J. P.; Winitz, M. Chemistry of the Amino Acids; Wiley: New York, 1961; Vol. 1; p 569.
7. For reviews, see: (a) Scarborough, R. M.; Gretler, D. D. J. Med. Chem. 2000, 43, 3453.
8. (b) Mousa, S. A. Drug Discovery Today 1999, 4, 552.
9. Miller, W. H.; Ku, T. W.; Ali, F. E.; Bondinell, W. E.; Calvo, R. R.; Davis, L. D.; Erhard, K. F.; Hall, L. B.; Huffman, W. F.; Keenan, R. M.; Kwon, C.; Newlander, K. A.; Ross, S. T.; Samanen, J. M.; Takata, T. D.; Yuan, C. Tetrahedron Lett. 1995, 36, 9433.
10. Hayes, J. F. Synlett 1999, 865.
11. Etridge, S. K.; Hayes, J. F.; Walsgrove, T. C.; Wells, A. S. Org. Process Res. Dev. 1999, 3, 60.
12. Takeda, K.; Akiyama, A.; Nakamura, H. Synthesis 1994, 1063.