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Categories: C-C Bond Formation > Cyclic compounds > Cycloalkenes

Synthesis of 1,4-cyclohexadienes

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Diels-Alder Reaction


Recent Literature


The cobalt-catalyzed Diels-Alder reaction of alkynyl pinacol boronic esters with various dienes generates cycloadducts in very good regioselectivity. A reaction sequence (Diels-Alder reaction, Suzuki coupling, DDQ oxidation) was successfully performed as a one pot operation without isolation of the intermediates.
G. Hilt, K. I. Smolko, Angew. Chem. Int. Ed., 2003, 42, 2795-2797.


Aryne Diels-Alder reactions with functionalized acyclic dienes give useful cis-substituted dihydronaphthalene building blocks in good yield. Asymmetric aryne cycloadditions with Oppolzer's sultam as a chiral auxiliary are also reported .
C. Dockendorff, S. Sahli, M. Olsen, L. Milhau, M. Lautens, J. Am. Chem. Soc., 2005, 127, 15028-15029.


Ammonia Free Partial Reduction of Aromatic Compounds Using Lithium Di-tert-butylbiphenyl (LiDBB)
T. J. Donohoe, D. House, J. Org. Chem., 2002, 67, 5015-5018.