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

Synthesis of cyclohexanones


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.

Development of (Trimethylsilyl)ethyl Ester Protected Enolates and Applications in Palladium-Catalyzed Enantioselective Allylic Alkylation: Intermolecular Cross-Coupling of Functionalized Electrophiles
C. M. Reeves, D. C. Behenna, B. M. Stotz, Org. Lett., 2014, 16, 2314-2317.

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.

Ligand-free cationic Pd(II) catalyst is a highly active catalytic system for conjugate additions of boroxines to sterically hindered γ-substituted cyclohexenones in the presence of NaNO3 as an additive. More challenging γγ- and βγ-substrates also react well to produce products with quaternary centers in a highly diastereoselective fashion.
J. A. Jordan-Hore, J. N. Sanderson, A.-L. Lee, Org. Lett., 2012, 14, 2508-2511.

Pyrrolidinine-thioxotetrahydropyrimidinone derivatives were tested for their catalytic properties in various asymmetric organic transformations. These catalysts could efficiently catalyze the reactions in brine, without the use of organic solvent, and by employing an almost stoichiometric amount of reagents. Thus, the products were isolated by simple extractions in excellent yields, diastereoselectivities, and enantioselectivities.
N. Kaplaneris, G. Koutoulogenis, M. Raftopoulou, C. G. Kokotos, J. Org. Chem., 2015, 80, 5464-5473.

A fluorous (S)-pyrrolidine sulfonamide organocatalyst promotes highly enantio- and diastereoselective Michael addition reactions of ketones and aldehydes with nitroolefins in water. The organocatalyst is conveniently recovered from the reaction mixtures by fluorous solid-phase extraction and can be reused.
L. Zu, J. Wang, H. Li, W. Wang, Org. Lett., 2006, 8, 3077-3079.

Two new atropisomeric electron-poor chiral diphosphine ligand analogues of SYNPHOS were prepared, that allow a highly performant Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds at room temperature.
F. Berhal, O. Esseiva, C.-H. Martin, H. Tone, J.-P. Genet, T. Ayad, V. Ratovelomanana-Vidal, Org. Lett., 2011, 13, 2806-2809.

Cyclohexane-1,3-dione derivatives synthesis from unreactive acetone has been accomplished through a consecutive Michael-Claisen process. Furthermore, the scope of different carbonyl compounds was investigated and resulted with similar consecutive Michael-Claisen process for CDD synthesis. The reaction exhibited remarkable regioselectivity in Michael addition followed by Claisen cyclization.
D. Sharma, Bandna, A. K. Shil, B. Singh, P. Das, Synlett, 2012, 23, 1199-1204.

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.

A simple chiral primary amine catalyses a highly efficient reaction for the synthesis of both Wieland-Miescher ketone and Hajos-Parrish ketone as well as their analogues in high enantioselectivity and excellent yields. This procedure represents one of the most efficient methods for the synthesis of these versatile chiral building blocks even in gram scale with 1 mol% catalyst loading.
P. Zhou, L. Zhang, S. Luo, J.-P. Cheng, J. Org. Chem., 2012, 77, 2526-2530.