Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating complexity from simplicity

内炔的串联硅烷基甲酰化-巴豆基硅烷化/Tamao氧化:由简单生成复杂性的杰出范例

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Abstract

The rhodium-catalyzed tandem silylformylation-crotylsilylation reaction has been extended to include internal alkynes. Tamao oxidation of the initial product leads to the production of a substituted enol, which undergoes highly diastereoselective tautomerization. The resulting one-pot procedure fashions three new stereocenters, a ketone, and a terminal alkene from a butenyl group, a propynyl group, a silyl hydride, H2O2, and CO.

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