Iron Porphyrin-Catalyzed Olefination of Ketenes with Diazoacetate for the Enantioselective Synthesis of Allenes

Chuan-Ying Li,† Xiao-Bing Wang,‡ Xiu-Li Sun,† Yong Tang,*† Jun-Cheng Zheng,† Zheng-Hu Xu,† Yong-Gui Zhou,*‡ and Li-Xin Dai†;
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, and Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China
J. Am. Chem. Soc., 2007, 129 (6), pp 1494–1495
DOI: 10.1021/ja068642v
Publication Date (Web): January 18, 2007
Copyright © 2007 American Chemical Society
†

 Shanghai Institute of Organic Chemistry.

,
‡

 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.

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

Abstract

Abstract Image

In the presence of Ph3P and catalytic Fe(TCP)Cl, ketenes could react with EDA to give allenes in high yields under neutral conditions for the first time. By employing chiral phosphine instead of PPh3, allenes could be synthesized with high enantioselectivity (93−98% ee) in good yields.

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History

  • Published In Issue February 14, 2007
  • Received December 1, 2006

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