Synthesis of cycloalkenes

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Recent Literature

An oxidation-methylenation one-pot procedure in the presence different catalysts produced terminal alkenes in high yields. A methylenation-ring-closing process for the synthesis of cyclic alkenes from carbonyl derivatives was even expanded with an initial oxidation to allow the use of alcohols as substrates.
H. Lebel, V. Paquet, J. Am. Chem. Soc., 2004, 126, 11152-11153.

The GaCl₃-catalyzed skeletal reorganization of enynes is simple and provides a diverse range of dienes in good to high yields. The reaction of enynes proceeds in a stereospecific manner with respect to the geometry of the olefin moiety.
N. Chatani, H. Inoue, T. Kotsuma, S. Murai, J. Am. Chem. Soc., 2002, 124, 10294-10295.

A mild, palladium-catalyzed intramolecular oxidative alkylation of various ζ-alkenyl β-diketones and ζ-alkenyl β-keto esters in the presence of CuCl₂ at room temperature formed the corresponding 2-cyclohexenones in high yield.
T. Pei, X. Wang, R. A. Widenhoefer, J. Am. Chem. Soc., 2003, 125, 648-649.

An efficient and regioselective Yb(OTf)₃-promoted palladium-catalyzed oxidative cyclization of γ-heteroalkenyl β-keto amides has been developed. Under simple aerobic condition, various six-, seven-, and eight-membered-ring N- and O-heterocycles were obtained in excellent yield.
K.-T. Yip, J.-H. Li, O.-Y. Lee, D. Yang, Org. Lett., 2005, 7, 5717-5719.

Cycloalkenes can be efficiently prepared by a new Ru-catalyzed decarbonylative cyclization of terminal alkynals. Under appropriate conditions, cycloisomerizations to conjugated aldehydes may be observed. Both processes involve catalytic Ru vinylidenes.
J. A. Varela, C. Gonzlez-Rodríguez, S. G. Rubín, L. Castedo, Carlos Saá, J. Am. Chem. Soc., 2006, 128, 9576-9577.

J. A. Varela, C. Gonzlez-Rodríguez, S. G. Rubín, L. Castedo, Carlos Saá, J. Am. Chem. Soc., 2006, 128, 9576-9577.

The use of cationic silver (AgSbF₄) as a catalyst for intra- and intermolecular alkyne-carbonyl coupling is described.
J. U. Rhee, M. J. Krische, Org. Lett., 2005, 7, 2493-2495.

A sequence of two gold(I)-catalyzed isomerization steps allows the synthesis of functionalized acetoxy bicyclo[3.1.0]hexenes from 5-en-2-yn-1-yl acetates. Acetoxy bicyclo[3.1.0]hexene products can be further transformed to 2-cycloalkenones by simple methanolysis.
A. Buzas, F. Gagosz, J. Am. Chem. Soc., 2006, 128, 12614-12615.

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A novel Rh(II)-catalyzed enantioselective [2 + 1]-cycloaddition of ethyl diazoacetate to terminal acetylenes and olefins with high enantioselectivity is described. The catalyst, which is readily available, robust, and effective, can be recovered and reused.
Y. Lou, M. Horikawa, R. A. Kloster, N. A. Hawryluk, E. J. Corey, J. Am. Chem. Soc., 2004, 126, 8916-8918.

[ReBr(CO)₃(thf)]₂ catalyzes the reaction of a 1,3-dicarbonyl cyclic compound with an acetylene to give a medium-sized cyclic compound in excellent yield. By using isocyanide as an additive, the insertion of acetylenes into a carbon-carbon single bond occurs under mild conditions.
Y. Kuninobu, A. Kawata, K. Takai, J. Am. Chem. Soc., 2006, 128, 11368-11369.

The reaction of organocerium reagents, generated in situ from aryl and heteroaryl lithium compounds, with cycloalkanones proceeds cleanly to provide alkoxides. Addition of MsCl or SOCl₂ with DBU gave aryl-substituted cycloalkenes in good yields. A short total synthesis of (±)-laurokamurene B is described.
J. Tallineau, G. Bashiardes, J.-M. Coustard, F. Lecornué, Synlett, 2009, 2761-2764.