Development of Chiral Spiro P-N-S Ligands for Iridium-Catalyzed Asymmetric Hydrogenation of β-Alkyl-β-Ketoesters.

Angew Chem Int Ed Engl

State Key Laboratory and Institute of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071 (China) http://zhou.nankai.edu.cn.

Published: July 2015

AI Article Synopsis

  • Scientists created new chiral ligands called spiro P-N-S ligands (SpiroSAP) and made iridium complexes using them.
  • By adding a 1,3-dithiane group to these ligands, they developed an effective chiral iridium catalyst.
  • This catalyst was successful in asymmetric hydrogenation of β-alkyl-β-ketoesters, yielding chiral β-alkyl-β-hydroxyesters with very high enantioselectivities (95-99.9% ee) and impressive turnover numbers (up to 355,000).

Article Abstract

The chiral tridentate spiro P-N-S ligands (SpiroSAP) were developed, and their iridium complexes were prepared. Introduction of a 1,3-dithiane moiety into the ligand resulted in a highly efficient chiral iridium catalyst for asymmetric hydrogenation of β-alkyl-β-ketoesters, producing chiral β-alkyl-β-hydroxyesters with excellent enantioselectivities (95-99.9% ee) and turnover numbers of up to 355,000.

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Source
http://dx.doi.org/10.1002/anie.201502860DOI Listing

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