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Gandon, V.; Thorimbert, S.; Malacria, M., Science of Synthesis, (2009) 46, 228.
The palladium-catalyzed cycloisomerization of 1,6- and 1,7-enynes into 1,3-dienes having endocyclic and exocyclic double bonds was first reported in 1994.[187] For example, both the cyclopentene 192 and the cyclohexene 193 can be synthesized from the 1,6-enyne 190 in good yields. The ligand bonded to the palladium atom is responsible for the chemical course of the reaction. Thus, in the presence of the ligand 1,3-bis(diphenylphosphino)propane isomerization of the initially formed 1,2-bis(methylene)cyclopentene 191 affords the cyclopentene 192 (Scheme 68), a result that has been confirmed during studies directed at the synthesis of cyclic amino acids.[188] The use of a catalytic system composed of palladium(II) acetate (40 mol%) and tri-2-tolylphosphine (80 mol%) in acetic acid/acetonitrile can be utilized for the preparations of macrocyclic peptides, but yields are moderate.[189]
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References
| [187] | Meeee, M. M.; Mee, M.; Mee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [188] | Møeeee, M.; Meeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [189] | Meeeeee, M.; Mee, M. M.; Meeee, M. M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
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