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-Reference-Cited by-同舟云学术

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

Published:2001-07-14 Issue:16 Volume:3 Page:2583-2586
ISSN:1523-7060
Container-title:Organic Letters
language:en
Short-container-title:Org. Lett.

Author:

Ma Dawei¹,Xia Chengfeng¹

Affiliation:

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

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/ol016258r

Reference11 articles.

1. Tetrahedron report number 163

2. Accelerating Effect Induced by the Structure of α-Amino Acid in the Copper-Catalyzed Coupling Reaction of Aryl Halides with α-Amino Acids. Synthesis of Benzolactam-V8

3. (a) Davies, S. G.; Ichihara, O.Tetrahedron: Asymmetry,1991,2, 183.

4. Asymmetric synthesis of syn-α-alkyl-β-amino acids

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 correspondingN-aryl β-amino acid.

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