Silicon-assisted propargylic transfer to aldehydes.
A new and efficient method of obtaining homopropargylic alcohols via homopropargylic transfer from the allenic alcohol to various aldehydes in the presence of Lewis acid catalysts is described; stereochemical studies have shown that this process is the first oxonium [3,3]-sigmatropic rearrangement of an allenic alcohol to a homopropargylic alcohol in the presence of aldehydes and Lewis acid.
Lee
Kiew-Ching
KC
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
Lin
Man-Jing
MJ
Loh
Teck-Peng
TP
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*
D000447:Aldehydes; D000480:Alkynes; D020005:Propanols; C028255:propargyl alcohol; D012825:Silicon