ChemInform Abstract: Reactions of Carbonyl Compounds with ((Trimethylsilyl)propargyl) diisobutyltelluronium Bromide Mediated by Different Strong Bases: Highly Regioselective Synthesis of (Trimethylsilyl)propargyl Alcohol and Highly Stereoselective Synthesis of cis-(Trimethylsilyl)alkynyl Epoxides.
Abstract
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ChemInform Abstract
Addition reaction of 3-bromo-1-(trimethylsilyl)-1-propyne (II) with diisobutyl telluride (I) gives the salt (III) mentioned in the title. Further lithiation with n-butyllithium and quenching with the carbonyl compounds (IV) produces the propargylic alcohols (V). However, when the lithiation is carried out with nonnucleophilic bases such as LDA or lithium 2,2,6,6-tetramethylpiperidide, the subsequent addition reaction with the carbonyl compounds (IVa) and (IVc) results in the stereoselective formation of the oxiranes (VI).
