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Iron-Catalyzed Highly Regio- and Stereoselective Conjugate Addition of 2,3-Allenoates with Grignard Reagents

Zhan Lu, Guobi Chai and Shengming Ma*

*Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, PR China, Email:

Z. Lu, G. Chai, S. Ma, J. Am. Chem. Soc., 2007, 129, 14546-14547.

DOI: 10.1021/ja075750o

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An efficient highly regio- and stereoselective iron-catalyzed conjugate addition of 2,3-allenoates with primary or secondary alkyl, phenyl, or vinyl Grignard reagents gives multi-substituted β,γ-unsaturated enoates in good yields. The in situ formed magnesium dienolate may readily react with different electrophilic reagents to construct an allylic quaternary carbon at the α-position of the ester group.

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Key Words

Conjugate Addition, Alkenes

ID: J48-Y2007-3750