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