title: Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating complexity from simplicity.
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.
authors.affiliation: Department of Chemistry, Columbia University, New York, New York 10027, USA.
authors.forename: Jared T
authors.initials: JT
authors.lastname: Spletstoser
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Zacuto
authors.forename: James L
authors.initials: JL
authors.lastname: Leighton
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*
chemical_list: D000480:Alkynes; D012821:Silanes; D012238:Rhodium