Molecules (Dec 2013)

Highly Enantioselective Addition of Phenylethynylzinc to Aldehydes Catalyzed by Chiral Cyclopropane-Based Amino Alcohols

  • Bing Zheng,
  • Zhiyuan Li,
  • Feipeng Liu,
  • Yanhua Wu,
  • Junjian Shen,
  • Qinghua Bian,
  • Shicong Hou,
  • Ming Wang

DOI
https://doi.org/10.3390/molecules181215422
Journal volume & issue
Vol. 18, no. 12
pp. 15422 – 15433

Abstract

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The enantioselective addition of phenylethynylzinc to aldehydes catalyzed by a series of cyclopropane-based amino alcohol ligands 7 was investigated. The reactions afforded chiral propargylic alcohols in high yields (up to 96%) and with excellent enantioselectivities (up to 98% ee) under mild conditions. Furthermore, studies on the structural relationship show that the matching of the chiral center configuration is crucial to obtain the high enantioselectivity.

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