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The cobalt-catalyzed homo Diels-Alder reaction of norbornadiene and terminal acetylenes yields chiral deltacyclenes. We tried to extend the scope of this reaction to acetylenes containing a heteroatom (i) in the propargylic position, (ii) in the ortho position of phenylacetylene or (iii) directly bonded to the triple bond. The synthesis of nine new substituted deltacyclenes with cobalt catalysts...