• Prof. Wesley A. Chalifoux (University of Nevada-Reno, USA)

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Diels–Alder Reaction of Conjugated 2,4-Diynones with Dienes Yields 2-Alkynyl-1,4-cyclohexadienes

Wesley Chalifoux and co-workers report the synthesis of 2-alkynyl-1,4-cyclohexadienes via a Diels–Alder reaction.

Synthesis of 2-Alkynyl-1,4-cyclohexadienes via a Diels–Alder Reaction of Conjugated 2,4-Diynones: K. B. Hamal, R. Bam, W. A. Chalifoux
Synlett 2016, 27, DOI:10.1055/s-0035-1561451

Highly functionalized cyclic molecules are of great interest as intermediates for the synthesis of natural and bioactive products, as well as drugs. The Diels–Alder reaction is an ideal method for the construction of six-membered cyclic products but the use of alkynes as dienophiles is quite uncommon. Recently, the group of Professor W. A. Chalifoux at the University of Nevada-Reno (USA) reported an effective method for accessing complex and highly functionalized 2-alkynyl-1,4-cyclohexadienes by means of Me2AlCl-catalyzed Diels–Alder reaction of different dienes with conjugated 2,4-diynones.

 

  • Diels–Alder reaction of conjugated 2,4-diynones with dienes

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Professor Chalifoux said: “The use of readily available high-energy polyyne starting materials allowed us to arrive at more complex and functionally useful cyclic ‘skipped’ diene intermediates on the way to biologically relevant molecules.”
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