Categories: C-C Bond Formation > Oxygen-containing molecules > α,β-unsaturated compounds >
Synthesis of substituted α,β-unsaturated compounds
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Recent Literature
Iron-catalyzed cross-coupling of Grignard reagents with (E)- and (Z)-enol
tosylates proceeded smoothly to give a variety of the corresponding (E)-
and (Z)-trisubstituted α,β-unsaturated methyl esters in good yield. The
simple, mild, stereoretentive method utilized iron(III) chloride and other iron
salts as catalyst.
H. Nishikado, H. Nakatsuji, K. Ueno, R. Nagase, Y. Tanabe, Synlett, 2010,
2087-2092.
A Pd-catalyzed oxidative cross-coupling reaction of arylboronic acids with
α-diazoesters using molecular oxygen as the reoxidant gives E-α,β-diarylacrylates
in good yields and very high E-to-Z selectivity.
Y.-T. Tsoi, Z. Zhou, A. S. C. Chan, W.-Y. Yu, Org. Lett., 2010,
12, 4506-4509.
A ruthenium-catalyzed chelation-assisted C-H bond activation of aromatic ketones
followed by reaction with olefins provides Heck-type products in good to
excellent yields with a high regio- and stereoselective manner.
K. Padala, M. Jeganmohan, Org. Lett., 2011,
13, 6144-6147.
A copper-catalzed functionalization of propiolate esters with various Grignard
reagents in presence of trimethylsilyl trifluoromethanesulfonate enables the
synthesis of substituted E-vinyl silanes in good yields and excellent
diastereoselectivities via a catalytic carbocupration-silicon group migration
sequence.
A. J. Mueller Hendrix, M. P. Jennings, Org. Lett., 2010,
12, 2750-2753.
A stereoselective approach towards ethyl-substituted conjugated dienoic esters
utilising a Suzuki cross-coupling reaction has been achieved. In addition, a
method for their conversion into the corresponding ethyl ketones is presented.
D. Keck, T. Muller, S. Bräse, Synlett, 2006,
3457-3460.
A radical carbozincation of diethyl acetylenedicarboxylate in the presence of
air leads to fumaric derivatives through a selective alkylzinc group radical
transfer controlled by coordination. The total trans stereocontrol is
unprecedented, carbocupration is well-known to give the reversal selectivity at
low temperature, while classical radical addition methodologies lead to mixtures
of isomers.
J. Maury, L. Feray, M. P. Bertrand, Org. Lett., 2011,
13, 1884-1887.
N-heterocyclic carbenes catalyze intramolecular β-alkylations of
α,β-unsaturated esters, amides, and nitriles that bear pendant leaving
groups to form a variety of ring sizes. The mechanism is discussed.
C. Fischer, S. W. Smith, D. A. Powell, G. C. Fu, J. Am. Chem. Soc.,
2006,
128, 1472-1473.
Highly regioselective Heck couplings of α,β-unsaturated tosylate and mesylate
derivatives with N-acyl N-vinylamines and vinyl ethers were
achieved. This method provides a cheap alternative to similar couplings using a
triflate electrophile.
A. L. Hansen, T. Skrydstrup, Org. Lett.,
2005,
7, 5585-5587.
A. L. Hansen, T. Skrydstrup, Org. Lett.,
2005,
7, 5585-5587.
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Copper-Catalyzed Conjugate Addition to α,β-Unsaturated Carbonyl Compounds |
