Halogenation of α-trimethylsilyl β,γ-unsaturated esters has the ability to be a versatile handle for natural product synthesis. α,β-unsaturated esters are utilized as intermediates in multi-step organic synthesis. The goal of this work is to explore electrophilic halogenation of α-trimethylsilyl β,γ-unsaturated esters through a multi-step route. Initial synthetic steps including stereoselective TMSOTf-mediated catalytic carbocupration of ethyl propiolate, followed by deconjugation of the α,β-substituted vinyl silanes, and halogenation of the resulting α-trimethylsilyl β,γ-unsaturated esters have been successful.

Halogenation of α-trimethylsilyl-β,γ-unsaturated esters

255th National Meeting (2018)

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