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Synthesis of substituted carboxylic acids, esters and amides

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An efficient cobalt-catalyzed reductive coupling reaction of alkyl halides with alkenes bearing electron-withdrawing groups in the presence of water and zinc powder in acetonitrile gave the corresponding Michael-type addition products in high yields. The mechanism is discussed.
P. Shukla, Y.-C. Hsu, C.-H. Cheng, J. Org. Chem., 2006, 71, 655-658.


Tin-free Giese reaction of alkyl iodides with electron-deficient alkenes and the related radical carbonylation process proceeded efficiently in the presence of sodium cyanoborohydride and tetrabutylammonium cyanoborohydride. Transfer of iodine followed by hydride reduction of the resulting carbon-iodine bond is proposed as a possible mechanism.
I. Ryu, S. Uehara, H. Hirao, T. Fukuyama, Org. Lett., 2008, 10, 1005-1008.


Inexpensive and readily available Grignard reagents and stable dinuclear Cu complexes can be used for the catalytic enantioselective conjugate addition to simple acyclic α,β-unsaturated methyl esters providing β-substituted chiral esters in good yields and with excellent enantioselectivities.
F. Lopez, S. R. Harutyunyan, A. Meetsma, A. J. Minnaard, B. L. Feringa, Angew. Chem. Int. Ed., 2005, 44, 2752-2756.


F. Lopez, S. R. Harutyunyan, A. Meetsma, A. J. Minnaard, B. L. Feringa, Angew. Chem. Int. Ed., 2005, 44, 2752-2756.


A highly efficient regio- and enantioselective catalytic asymmetric addition of Grignard regeants to α,β-unsaturated esters is promoted by the CuI-Tol-BINAP system.
S.-Y. Wang, S.-J. Ji, T.-P. Loh, J. Am. Chem. Soc., 2007, 129, 276-277.


A highly efficient regio- and enantioselective catalytic asymmetric addition of Grignard regeants to α,β-unsaturated esters is promoted by the CuI-Tol-BINAP system.
S.-Y. Wang, S.-J. Ji, T.-P. Loh, J. Am. Chem. Soc., 2007, 129, 276-277.


An additive-free, clean conjugate addition reaction of organosiloxanes to α,β-unsaturated compounds is catalyzed by a cationic rhodium complex in dioxane/water. The mechanism involves a transmetalation step between the rhodium complex and the silicon reagent.
S. Oi, Y. Honma, Y. Inoue, Org. Lett., 2002, 4, 667-669.


A conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds catalyzed by a cationic rhodium complex generated from [Rh(cod)(MeCN)2]BF4 and (S)-BINAP in dioxane/water gave products in good yields and excellent enantioselectivities.
S. Oi, A. Taira, Y. Honma, Y. Inoue, Org. Lett., 2003, 5, 97-99.


A nickel catalyst system for 1,4-addition of trialkylboranes to α,β-unsaturated esters has been developed. For the alkylation reaction with 9-alkyl-9-BBNs, addition of methanol was found to be essential.
K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett., 2007, 9, 1541-1544.


The use of Me-StackPhos as ligand enables a Cu-catalyzed enantioselective conjugate alkynylation of Meldrum’s acid acceptors. The reaction tolerates a wide range of alkynes furnishing highly useful β-alkynyl Meldrum's acid building blocks in high yields and excellent enantioselectivity.
S. Mishra, J. Liu, A. Aponick, J. Am. Chem. Soc., 2017, 139, 3352-3355.


A (Salen)Al-Cl complex catalyzes the asymmetric conjugate addition of hydrogen cyanide to α,β-unsaturated imides in high yields and enantioselectivities. The cyanide adducts can readily be converted into a variety of useful chiral building blocks, including α-substituted-β-amino acids.
G. M. Sammis, E. N. Jacobsen, J. Am. Chem. Soc., 2003, 125, 4442-4443.


Chiral complexes of calcium promote asymmetric 1,4-addition reactions and [3+2] cycloaddition reactions of α-amino acid derivatives with α,β-unsaturated carbonyl compounds. The reactions proceeded smoothly in the presence of 5-10 mol % of the chiral calcium catalyst to afford the desired adducts in high yields with high diastereo- and enantioselectivities.
S. Saito, T. Tsubogo, S. Kobayashi, J. Am. Chem. Soc., 2007, 129, 5364-5365.


The conversion of β-keto esters into β-methylated and phenylated γ-keto esters can be achieved through treatment with zinc carbenoids derived­ from 1,1-diiodoethane and diiodotoluene, respectively.
W. Lin, R. J. McGinness, E. C. Wilson, C. K. Zercher, Synthesis, 2007, 2404-2408.


A TiCl4-Mg promoted coupling of various amides with CH2Cl2 and methyl acrylate allows an extremely simple and practical synthesis of 1,5-keto esters. The efficiency of this chemistry is illustrated by the very simple preparation of unusual 4,4-dideuterio-1,5-keto esters using CD2Cl2.
K.-W. Lin, C. Y. Chen, W.-F. Chen, T.-H. Yan, J. Org. Chem., 2008, 73, 4759-4761.


Novel chiral phosphine-olefin ligands have been designed, which act as bidentates in an efficient rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to maleimides.
R. Shintani, W.-L. Duan, T. Nagano, A. Okada, T. Hayashi, Angew. Chem. Int. Ed., 2005, 44, 4611-4614.


R. Shintani, W.-L. Duan, T. Nagano, A. Okada, T. Hayashi, Angew. Chem. Int. Ed., 2005, 44, 4611-4614.


An efficient and practical Cu-catalyzed asymmetric conjugate addition of dialkylzinc reagents to tetrasubstituted cyclic enones afforded quaternary all-carbon stereogenic centers in up to 95% ee. The products can be readily functionalized to afford various synthetically versatile compounds in high optical purity.
A. W. Hird, A. H. Hoveyda, J. Am. Chem. Soc., 2005, 127, 14988-14989.


The efficiency of the photoinduced radical addition of tertiary amines to olefinic double bonds is significantly enhanced and the stereoselectivity is influenced when thiocarbonyl compounds are added to the reaction mixture.
D. Harakat, J. Pesch, S. Marinkovic, N. Hoffmann, Org. Biomol. Chem., 2006, 4, 1202-1205.


Silyloxyallenes serve as highly useful α-acylvinyl anion equivalents, that undergo conjugate additions to alkylidene malonates in the presence of Sc(OTf)3 as catalyst. The reaction delivers intermolecular Rauhut-Currier products in excellent yields and regioselectivities for a wide scope of substrates.
T. E. Reynolds, M. S. Binkley, K. A. Scheidt, Org. Lett., 2008, 10, 2449-2452.


An efficient highly regio- and stereoselective iron-catalyzed conjugate addition of 2,3-allenoates with primary or secondary alkyl, phenyl, or vinyl Grignard reagents gives multi-substituted β,γ-unsaturated enoates in good yields. The in situ formed magnesium dienolate may readily react with different electrophilic reagents to construct an allylic quaternary carbon at the α-position of the ester group.
Z. Lu, G. Chai, S. Ma, J. Am. Chem. Soc., 2007, 129, 14546-14547.