Categories: C-C Bond Formation > Cyclic compounds > Cyclic ketones
Synthesis of cyclohexanones
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Recent Literature
tert-Dodecanthiol-catalyzed generation of acyl radicals and their
intramolecular addition to double bonds gave 2-substituted five- and
six-membered cyclic ketones in good yields.
K. Yoshikai, T. Hayama, K. Nishimura, K.-I. Yamada, K. Tomioka, J. Org. Chem.,
2005, 70, 681-683.
In the presence of PdCl2(MeCN)2, CuCl2, and
PEG-400, various alkenyl β-keto esters and amides underwent a selective
cyclization to give six-membered carbocycles in good to excellent yields. The
PdCl2(MeCN)2/CuCl2/PEG-400 system could be
recycled and reused five times without any loss of catalytic activity.
J.-H. Li, Q.-M. Zhu, Y. Liang, D. Yang, J. Org. Chem., 2005, 70,
5347-5349.
The reaction of β-keto esters with CF3CO2ZnCH2I
provided the corresponding chain-extended products in moderate to good
yields. α-Substituted acyclic β-keto esters reacted less efficiently than
cyclic β-keto esters or simple β-keto esters.
S. Xue, Y.-K. Liu, L.-Z. Li, Q.-X. Guo, J. Org. Chem., 2005,
70, 8245-8247.
An Efficient and Scalable One-Pot Double Michael Addition-Dieckmann
Condensation for the Synthesis of 4,4-Disubstituted Cyclohexane β-Keto Esters
M. R. DeGraffenreid, S. Bennett, S. Caille, F. Gonzalez-Lopez de Turiso, R. W.
Hungate, L. D. Julian, J. A. Kaizerman, D. L. McMinn, D. Sun, X. Yan, J. P.
Powers, J. Org. Chem.,
2007,
72, 7455-7458.
