The Vinylogous Aldol Reaction:  A Valuable, Yet Understated Carbon−Carbon Bond-Forming Maneuver

Casiraghi, Giovanni; Zanardi, Franca; Appendino, Giovanni; Rassu, Gloria

doi:10.1021/cr990247i

Cited by 550 publications

(222 citation statements)

References 236 publications

(411 reference statements)

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“…The vinologous aldol reaction with the silyloxy diene furan synthon and the relevant aldehydes was the strategy utilized to prepare compounds 5-14 [18,20,[26][27][28][29]. Thus, treatment of lactones 2a or 2b with tert-butyldimethylsilyltrifluoromethanesulfonate (TBDMSOTf) and diisopropylethylamine (DIPEA) resulted in the formation of the furan 3, which was not isolated.…”

Section: Preparation Of Lactonesmentioning

confidence: 99%

Synthesis and Cytotoxic Activity of Some 3-Benzyl-5-Arylidenefuran-2(5H)-ones

et al. 2007

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3-Benzyl-furan-2(5H)-one (2a) and 3-(4-bromobenzyl)-furan-2(5H)-one (2b) were treated with TBDMSOTf and converted into the corresponding tert-butyldimethylsilylfuran ethers. These furans were further condensed with several aromatic aldehydes affording compounds 5-14 with general 3-benzyl-5-arylidene-furan-2(5H)-one structures in 31% to 98% yields. Such compounds are analogues of the naturally occurring nostoclide lactones, reported to present moderate cytotoxic activity. Compounds 5-14 were submitted to an in vitro bioassay against the HL-60, HCT-8, SF295 and MDA-MB-435 cancer cell lines using the MTT cytotoxicity assay.

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Section: Preparation Of Lactonesmentioning

confidence: 99%

Synthesis and Cytotoxic Activity of Some 3-Benzyl-5-Arylidenefuran-2(5H)-ones

et al. 2007

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“…On page 20642, left column, within the Abstract, lines [16][17][18], "Finally, we describe the extension of the dienamine catalysisinduced vinylogous nucleophilicity to the asymmetric γ-amination of cyclohexene carbaldehyde" should be removed from the article.…”

mentioning

confidence: 99%

Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis

Bencivenni

Galzerano

Mazzanti

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

184

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In spite of the many catalytic methodologies available for the asymmetric functionalization of carbonyl compounds at their α and β positions, little progress has been achieved in the enantioselective carbon–carbon bond formation γ to a carbonyl group. Here, we show that primary amine catalysis provides an efficient way to address this synthetic issue, promoting vinylogous nucleophilicity upon selective activation of unmodified cyclic α,β-unsaturated ketones. Specifically, we document the development of the unprecedented direct and vinylogous Michael addition of β-substituted cyclohexenone derivatives to nitroalkenes proceeding under dienamine catalysis. Besides enforcing high levels of diastereo- and enantioselectivity, chiral primary amine catalysts derived from natural cinchona alkaloids ensure complete γ-site selectivity: The resulting, highly functionalized vinylogous Michael adducts, having two stereocenters at the γ and δ positions, are synthesized with very high fidelity. Finally, we describe the extension of the dienamine catalysis-induced vinylogous nucleophilicity to the asymmetric γ-amination of cyclohexene carbaldehyde.

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“…The important building fragments of biological active compounds, biomaterials, polymers etc. are synthesized via aldol reaction [1]. Reaction of isophorone, which is a colourless-to-yellowish liquid, with a characteristic peppermint-like smell, with aldehyde yielded (E)-3-(2-chlorostyryl)-5,5-dimethylcyclohex-2-enone under basic conditions.…”

Section: Introductionmentioning

confidence: 99%

The Computational Study on (E)-3-(2-Chlorostyryl)-5,5-Dimethylcyclohex-2-Enone

et al. 2017

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A new isophorone derivative, (E)-3-(2-chlorostyryl)-5,5-dimethylcyclohex-2-enone, was synthesized by aldol reactions and characterized by single crystal diffraction method to determine the molecular structure. The computational analysis based on density functional theory with Becke's three-parameter hybrid functional was carried out using Lee, Yang and Parr correlation functional (B3LYP)/6-311++G(d,p), to investigate the structural parameters, the values of dipole moment, the total polarizability, the first-order hyperpolarizability for the non-linear optical behaviour and the thermodynamic parameters at different temperatures of the compound.

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The Vinylogous Aldol Reaction: A Valuable, Yet Understated Carbon−Carbon Bond-Forming Maneuver

Cited by 550 publications

References 236 publications

Synthesis and Cytotoxic Activity of Some 3-Benzyl-5-Arylidenefuran-2(5H)-ones

Synthesis and Cytotoxic Activity of Some 3-Benzyl-5-Arylidenefuran-2(5H)-ones

Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis

The Computational Study on (E)-3-(2-Chlorostyryl)-5,5-Dimethylcyclohex-2-Enone

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