Design of C2-Symmetric Tetrahydropentalenes as New Chiral Diene Ligands for Highly Enantioselective Rh-Catalyzed Arylation of N-Tosylarylimines with Arylboronic Acids

Zhi-Qian Wang,† Chen-Guo Feng,† Ming-Hua Xu,*†‡ and Guo-Qiang Lin*†
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China, and Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China
J. Am. Chem. Soc., 2007, 129 (17), pp 5336–5337
DOI: 10.1021/ja0710914
Publication Date (Web): April 11, 2007
Copyright © 2007 American Chemical Society
†

 Shanghai Institute of Organic Chemistry.

,
*

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

,
‡

 Shanghai Institute of Materia Medica.

, xumh@mail.sioc.ac.cn

Abstract

Abstract Image

A new type of C2-symmetric chiral diene ligand bearing a simple bicyclic [3.3.0] backbone was discovered. (3aS,6aS)-3,6-diphenyl-1,3a,4,6a-tetrahydropentalene was applied successfully in the Rh-catalyzed asymmetric arylation of N-tosylarylimines with arylboronic acids. With the new chiral diene ligand, a broad range of highly enantiomerically enriched diarylmethylamines (98−99% ee) as well as 3-aryl substituted phthalimidines (99% ee) could be easily prepared.

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History

  • Published In Issue May 02, 2007
  • Received February 14, 2007

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