Low Ligand Loading, Highly Enantioselective Addition of Phenylacetylene to Aromatic Ketones Catalyzed by Schiff-Base Amino Alcohols

Chao Chen,† Liang Hong,† Zhao-Qing Xu,† Lei Liu,† and Rui Wang*†‡
Department of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, Gansu 730000, China, and State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, China
Org. Lett., 2006, 8 (11), pp 2277–2280
DOI: 10.1021/ol060526+
Publication Date (Web): May 2, 2006
Copyright © 2006 American Chemical Society
†

 Lanzhou University.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
‡

 Chinese Academy of Sciences.

, wangrui@lzu.edu.cn

Abstract

Abstract Image

Schiff-base amino alcohols 7a,b derived from l-phenylglycine through three simple steps are found to be highly effective for the enantioselective addition of phenylacetylene to aromatic ketones. When the loading of 7b was 1 mol %, an ee value of up to 95% was obtained. However, when 7b was lowered to 0.1 mol %, a high ee value of 85% was still achieved. A practical solution to synthesize the optically active tertiary propargylic alcohols was described.

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History

  • Published In Issue May 25, 2006
  • Received March 3, 2006

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