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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

Dawei Ma* and Chengfeng Xia

*State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, 354 Fenglin Lu, Shanghai 200032, China

D. Ma, C. Xia, Org. Lett., 2001, 3, 2583-2586.

DOI: 10.1021/ol016258r

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β-Amino acids have an accelerating effect for the Ullmann-type aryl amination reaction: CuI-catalyzed coupling reactions of aryl halides with β-amino acids or β-amino esters are completed at 100C in 48 h. This coupling reaction can be used to prepare enantiopure N-aryl β-amino acids. An efficient synthesis of SB-214857, a potent GPIIb/IIIa receptor antagonist, is described.

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synthesis of SB-214857

Key Words

arylation, Ullmann coupling

ID: J54-Y2001