Hydrogen-Bonding Directed Reversal of Enantioselectivity

Wei Zeng,† Guo-Ying Chen,† Yong-Gui Zhou,*†‡ and Yu-Xue Li*‡;
Dalian Institute of Chemical Physics, CAS, 457 Zhongshan Lu, Dalian 116023, China, and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 354 Fenglin Lu, Shanghai 200032, China
J. Am. Chem. Soc., 2007, 129 (4), pp 750–751
DOI: 10.1021/ja067346f
Publication Date (Web): January 6, 2007
Copyright © 2007 American Chemical Society
†

 Dalian Institute of Chemical Physics.

,
*

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 Organic Chemistry.

, ygzhou@dicp.ac.cn, ; , liyuxue@mail.sioc.ac.cn

Abstract

Abstract Image

A successful stereochemical reversal was achieved in AgOAc catalyzed [3+2] cycloaddition by the formation of hydrogen bonding between ligand and reactant. This strategy provides an efficient and convenient route to prepare both enantiomers of a chiral compound. DFT studies proposed a reasonable mechanism of the reversal of the enantioselectivity; hydrogen bonding changed the transition state. The strategy may provide some useful hints for ligand design.

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History

  • Published In Issue January 31, 2007
  • Received October 12, 2006

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