Linchpin construction of unsymmetrical 1,4-alkynediols.
A one-pot preparation of unsymmetrical 1,4-alkynediols such as 2a by the coupling of trimethylsilylacetylene and two different aldehydes or ketones is reported. The dilithiated species 5 is generated by the sequential addition of the first aldehyde or ketone 1b to a solution of lithium trimethylsilylacetylide, followed by the addition of methyllithium, which removes the trimethylsilyl protecting group. Addition of the second aldehyde or ketone then leads to the unsymmetrical 1,4-alkynediol 2a.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@Udel.edu
Storck
Pierre H
PH
D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes; D000480:Alkynes / Q000138:chemical synthesis*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis*
D000438:Alcohols; D000447:Aldehydes; D000480:Alkynes; D000894:Anti-Inflammatory Agents, Non-Steroidal; D007659:Ketones