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, Email: tangymail.sioc.ac.cn

C.-Y. Li, X.-B. Wang, X.-L. Sun, Y. Tang, J.-C. Zheng, Z.-H. Xu, Y.-G. Zhou, L.-X. Dai, J. Am. Chem. Soc., 2007, 129, 1494-1495.

DOI: 10.1021/ja068642v

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Abstract

In the presence of Ph₃P and a catalytic amount of Fe(TCP)Cl, ketenes react with EDA to give allenes in high yields under neutral conditions. By employing a chiral phosphine, allenes could be synthesized with high enantioselectivity in good yields.

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Key Words

Allenes, TPP

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ID: J48-Y2007-0390