Cascade resulting in the reductive ethynylation of aldehydes: dissection of its components.
A mild and efficient two-carbon homologation of aldehydes exploiting multiple modes of KOt-Bu was developed. This process involves a sequential Peterson allenylation/allene-alkyne isomerization/protodesilylation in a single-flask operation. The differential roles played by the various elements of the process were demonstrated through dissection experiments.
Lee
Dongjoo
D
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10065, USA.
Danishefsky
Samuel J
SJ
D000447:Aldehydes / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry
D000447:Aldehydes; D000466:Alkadienes; D000480:Alkynes; D020005:Propanols; C006463:allyl alcohol; C025947:propadiene