Categories: C-C Bond Formation > Cyclic compounds > Cyclic ketones
Synthesis of cyclopentanones
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Recent Literature
Catalytic amounts of weak bases such as sodium carbonate can carry out the
ketonic decarboxylation of adipic acid into cyclopentanone selectively. This is
in accordance with a mechanism involving decarboxylation and nucleophilic attack
at a second carboxyl group. Stereogenic centres in the β-positions retain their
stereochemistry.
M. Renz, A. Corma, Eur. J. Org. Chem., 2004, 2036-2039.
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.
α-Aryl-α-diazo ketones derived from direct diazo transfer with α-aryl ketones cyclize efficiently
in the presence of Rh catalysts to give the
corresponding α-aryl cyclopentanones.
D. F. Taber, W. Tian, J. Org. Chem., 2007,
72, 3207-3210.
A ruthenium-catalyzed hydrative cyclization converts a range of 1,5-enynes
bearing terminal alkyne and Michael acceptor moieties into cyclopentanone
derivatives.
Y. Chen, D. M. Ho, C. Lee, J. Am. Chem. Soc., 2005, 127,
12184-12185.
A highly enantio- and diastereoselective intramolecular Stetter reaction has
been developed. Aliphatic and aromatic aldehydes and a broad range of
trisubstituted Michael acceptors have been found to afford the desired products
in good overall yield with high enantio- and diastereoselectivity.
J. Read de Alaniz, T. Rovis, J. Am. Chem. Soc., 2005, 127,
6284-6289.
The homologation of arylcyclobutanones with trimethylsilyldiazomethane gives
enolsilanes in the presence of Sc(OTf)3 as catalyst with a high
preference for methylene migration, whereas Sc(hfac)3 leads to
β-ketosilanes. Each adduct affords the cyclopentanone upon hydrolysis.
J. A. Dabrowski, D. C. Moebius, A. J. Wommack, A. F. Kornahrens, J. S. Kingsbury, Org. Lett., 2010,
12, 3598-3601.
Substituted carbocycles, tetrahydrofurans, and tetrahydropyrans can be
efficiently obtained from unsaturated carboxylic acids. The methodology involves
a Kolbe decarboxylation followed by an intramolecular radical cyclization and a
radicalradical cross-coupling process.
F.Lebreux, F. Buzzo, I. E. Markó, Synlett, 2008,
2815-2820.
A stereospecific gold(I)-catalyzed rearrangement of 1-alkynyl cyclobutanols and
cyclopropanols provides alkylidene cycloalkanones. The reaction tolerates
terminal alkynes as well as alkyl, aryl, and halo-substitution at the acetylenic
position and substituents on the ring.
J. P. Markham, S. T. Staben, F. D. Toste, J. Am. Chem. Soc., 2005,
127, 9708-9709.
Exposure of enynes containing a hydroxyl group at one of the propargylic
positions to catalytic amounts of either PtCl2 or (PPh3)AuCl/AgSbF6
results in a selective rearrangement with formation of bicyclo[3.1.0]hexan-3-one
derivatives. A total synthesis of the terpenes sabinone and sabinol is described.
V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc., 2004,
126, 8654-8655.
Cu-catalyzed asymmetric conjugate reduction of
β-substituted ketones leads to enantiomerically enriched
diphenylsilyl enol ethers, which are utilized in a diastereoselective Pd-catalyzed
α-arylation of various aryl bromides to yield disubstituted cycloalkanones with
excellent levels of enantiomeric and diastereomeric purity. The procedure can be
carried out in one-pot.
J. Chae, J. Yun, S. L. Buchwald, Org. Lett., 2004, 6, 4809-4812.
