Categories: C-C Bond Formation > Cyclic compounds > Cycloalkenes
Synthesis of cyclohexenes
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Name Reactions
Recent Literature
Using a catalytic amount of trialkylphosphines, alkyl halides undergo
efficient intramolecular Morita-Baylis-Hillman cyclization.
M. E. Krafft, K. A. Seibert, Synlett, 2006,
3334-3336.
An organomediated, intramolecular Morita-Baylis-Hillman reaction of molecules
bearing allylic leaving groups as the electrophilic partner provided a facile,
high yielding, straightforward synthesis of densely functionalized cyclic
molecules.
M. E. Krafft, T. F. N. Haxell, J. Am. Chem. Soc., 2005, 127,
10168-10169.
An efficient cycloallylation of mono-enone mono-allylic carbonates is achieved
upon exposure to tributylphosphine and 1 mol % Pd(Ph3P)4.
This transformation combines the nucleophilic features of the
Morita-Baylis-Hillman reaction with the electrophilic features of the
Trost-Tsuji reaction.
B. G. Jellerich, J.-R. Kong, M. J. Krische, J. Am. Chem. Soc., 2003,
125, 7758-7759.
A rhodium-catalyzed cycloisomerization converts various acyclic enynes to their
cyclic diene isomers with endoselectivity. Two different catalyst systems have
been developed, which are effective in promoting the C-C bond-forming
cyclization of enynes to furnish carbo- and heterocycles in good to excellent
yield. The mechanism is discussed.
H. Kim, C. Lee, J. Am. Chem. Soc., 2005, 127, 10180-10181.
The Diels-Alder cycloaddition of a variety of cyclic and open-chained dienes to
2-methacrolein and 2-bromoacrolein resulted in good yields and excellent
enantioselectivities by using a chiral indium complex.
Y.-Chua Teo, T.-P. Loh, Org. Lett., 2005, 7, 2539-2541.
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.
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.
