ChemInform Abstract: Tandem Silylformylation/Wittig Olefination of Terminal Alkynes: Stereoselective Synthesis of 2,4-Dienoic Esters.
Abstract
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ChemInform Abstract
A novel effective and straightforward approach to the synthesis of δ-silylated α,β,γ,δ-unsaturated esters (V) is presented, involving the one-pot tandem silylformylation—Wittig olefination reaction of terminal alkynes (I) with hydrosilanes (II), phosphonium ylides (III) and carbon monoxide (IV) in the presence of a cationic rhodium catalyst. The diene esters (V) are obtained in excellent stereoselectivity. The synthetic utility of these novel diene esters is demonstrated by [2 + 1] cycloaddition of diazomethane. The cyclopropanation takes place at the less substituted double bond and provides the corresponding cyclopropane adducts (VII) in high stereoselectivity.
