The substructures of many natural products and their precursors contain α, β’- β, γ- unsaturated esters. A highly stereoselective multistep single pot synthesis of said compounds was accomplished via a deconjugation, aldol, and stabilized Peterson olefination of a series of α-trialkylsilyl-β-alkyl-α, β -unsaturated esters. This procedure provided the newly formed alkenes at C3-C4 with an E/Z of &gt;20/1 and at C2-C3′ with a Z/E range of 12/1 to &gt;20/1. The ability to achieve these structures in a stereoselective manner should allow for the use of these motifs as unique precursors in organic synthesis, including the completion of natural products.

Stereoselective one-pot deconjugation, aldol, and stabilized Peterson olefination of α-trialkylsilyl-β-alkyl-α, β-unsaturated esters

2019 Spring National Meeting

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