Categories: C=C Bond Formation >
Synthesis of cycloalkenes
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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.
A sequence of Pd-catalyzed haloallylation of alkynes, Pd-catalyzed
cross-coupling, and Ru-catalyzed ring-closing metathesis enables a short
approach to various 1,2-disubstituted cyclopentadienes. The scope of the method
is broad.
N. Topolovčan, I. Panov, Martin Kotora, Org. Lett.,
2016, 18, 3634-3637.
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.