Iron-Catalyzed Diastereoselective Synthesis of α-(Methoxycarbonyl)allylsilanes

Authors

  • Guobi Chai,

    1. Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, P. R. China, Fax: +86-21-6260-9305
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  • Rong Zeng,

    1. Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, P. R. China, Fax: +86-21-6260-9305
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  • Chunling Fu,

    1. Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, P. R. China, Fax: +86-21-6260-9305
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  • Shengming Ma

    1. Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, P. R. China, Fax: +86-21-6260-9305
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Abstract

Stereodefined polysubstituted α-(methoxycarbonyl)allylsilanes were synthesized through iron-catalyzed conjugate additions between 1-(trimethylsilyl)allene-1-carboxylates and Grignard reagents in good to excellent yields. The use of Et2O as solvent for Grignard reagents was found to be very important for the diastereoselectivity of the reaction. Applications of the prepared allylic silanes for the stereocontrolled synthesis of α,β-alkenoates, a β,γ-alkenoate, and an allylic fluoride have been demonstrated.

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