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Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating
Jared T Spletstoser1, Michael J Zacuto, James L Leighton
1Department of Chemistry, Columbia University, New York, New York 10027, USA.
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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