Metal-free access to fully substituted skipped diynes. An efficient chemodifferentiating A2BB' 4CR manifold.
A metal-free chemodifferentiating A2BB' 4CR manifold for the modular synthesis of tertiary skipped diynes is described. The manifold performs a triethylamine triggered reaction of alkyl propiolates and acid chlorides to assemble two units of each component in the form of two propargylic alkynoates, a tertiary alcohol, and an ester. A differentiated incorporation of the two acid chloride components ensures functional diversity in the final structure. In addition, the presence of two connected propargylic alkynoates provides a reactive platform for complexity generation.
Tejedor
David
D
Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas, Astrofísico Francisco SAnchez 3, 38206 La Laguna, Tenerife, Spain. dtejedor@ipna.csic.es
López-Tosco
Sara
S
González-Platas
Javier
J
García-Tellado
Fernando
F
D002384:Catalysis; D053280:Diynes / Q000737:chemistry*; D008670:Metals / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry
D053280:Diynes; D008670:Metals; D009281:Naphthalenes; C110055:allenolic acid