Synfacts 2008(2): 0158-0158  
DOI: 10.1055/s-2007-992451
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Conjugate Addition of 2,3-Allenoates with Grignard Reagents

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
Z. Lu, G. Chai, S. Ma*
Zhejiang University, Hangzhou and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
23 January 2008 (online)


The authors describe the regio- and stereoselective addition of Grignard reagents to 2,3-allenoates to generate β,γ-unsaturated esters. This reaction proceeds with less than 5 mol% of an iron catalyst and gives the esters in high yields. This is an important contribution to synthetic chemistry in that it uses an inexpensive iron catalyst and readily available Grignard reagents.