Antimicrobial properties of Z-3-arenesulfonylpropenic acid esters

Araviiskii, R. A.; Veksler, V.I.; Grinberg, G. E.; Mikhailets, G. A.; Mikhailova, V. N.; Mikhailova, Margarita; Yakovlev, V. B.

doi:10.1007/bf00759057

Pharm Chem J

1988

DOI: 10.1007/bf00759057

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Antimicrobial properties of Z-3-arenesulfonylpropenic acid esters

R. A. Araviiskii¹,

V.I. Veksler²,

G. E. Grinberg³

et al.

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2016

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Regio- and Stereoselective Hydrosulfonation of Alkynylcarbonyl Compounds with Sulfinic Acid in Water

Yang

et al. 2016

J. Org. Chem.

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We report the atom-economic and environmentally friendly synthesis of Z-β-sulfonyl-a,β-unsaturated carbonyl compounds in water. The mechanism study reveals that the hydrosulfonylation of alkynylcarbonyl compounds with sulfinic acids proceeds via a mechanism that features a sulfinic acid molecule protonating an alkynyl motif to form the ethenium intermediate, which subsequently reacted with a sulfonyl anion to afford the desired products. The ethenium intermediate differentiated electronic and steric demands between the two substituents on the C≡C triple bond of the alkyne substrates to exhibit high regio- and stereoselectivity from a wide range of Z-β-sulfonyl-a,β-unsaturated carbonyl compounds.

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Regio- and Stereoselective Hydrosulfonation of Alkynylcarbonyl Compounds with Sulfinic Acid in Water

Yang

et al. 2016

J. Org. Chem.

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show abstract

Regioselective and stereoselective sulfonylation of alkynylcarbonyl compounds in water

Yin

Huang

et al. 2016

Green Chem.

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Antimicrobial properties of Z-3-arenesulfonylpropenic acid esters

Cited by 2 publications

References 2 publications

Regio- and Stereoselective Hydrosulfonation of Alkynylcarbonyl Compounds with Sulfinic Acid in Water

Regio- and Stereoselective Hydrosulfonation of Alkynylcarbonyl Compounds with Sulfinic Acid in Water

Regioselective and stereoselective sulfonylation of alkynylcarbonyl compounds in water

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