A versatile synthesis to trisubstituted nitroalkenes via nitroaldol reaction: Synthesis of Baylis-Hillman type adducts

A versatile synthesis to trisubstituted nitroalkenes via nitroaldol reaction: Synthesis of Baylis-Hillman type adducts

Pereira, Vera L. Patrocinio; Costa, Jeronimo da Silva; Silva, Alessandra C. de Souza e; Nascimento., Fernanda Cunha do

Abstract:

Electron deficient nitroalkenes consists of a versatile class of compounds reactives in Michael, Friedel- Crafts, Baylis-Hillman, Diels-Alder, Hetero-Diels- Alder, [3+2]-cycloaddition and Cross Coupling reactions. Usually, β-monosubstituted nitroalkenes and α,β-disubstituted nitroalkenes are synthesized via a nitroaldol reaction between an aldehyde and the nitromethane or a primary nitroalkane, respectively. The hydroxyl group elimination, in its free or active form, leads to the desired nitroalkene. Another usual route consists of nitration of the corresponding nitroalkene with toxic or volatile reagents leading to low regioselectivity. A more convenient method NaNO2–ceric ammonium nitrate has been reported. In the specific case of trisubstituted nitroalkenes, the nitroaldol route is not effective because of the high reversibility of nitroaldol reaction when ketones are employed.

Electron deficient nitroalkenes consists of a versatile class of compounds reactives in Michael, Friedel- Crafts, Baylis-Hillman, Diels-Alder, Hetero-Diels- Alder, [3+2]-cycloaddition and Cross Coupling reactions. Usually, β-monosubstituted nitroalkenes and α,β-disubstituted nitroalkenes are synthesized via a nitroaldol reaction between an aldehyde and the nitromethane or a primary nitroalkane, respectively. The hydroxyl group elimination, in its free or active form, leads to the desired nitroalkene. Another usual route consists of nitration of the corresponding nitroalkene with toxic or volatile reagents leading to low regioselectivity. A more convenient method NaNO2–ceric ammonium nitrate has been reported. In the specific case of trisubstituted nitroalkenes, the nitroaldol route is not effective because of the high reversibility of nitroaldol reaction when ketones are employed.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013819161427

Referências bibliográficas

• [1] 1 Averina, B. E. et al. Tetrahedron. Lett. 2011, 52, 2910–2913.
• [2] 2 Pereira, V.L.P. et al. Beilstein J. Org. Chem 2013, 9, 832-837.
• [3] 3 Pereira,V.L.P. et al. Beilstein J. Org. Chem 2013, 9, 838-845.

Como citar:

Pereira, Vera L. Patrocinio; Costa, Jeronimo da Silva; Silva, Alessandra C. de Souza e; Nascimento., Fernanda Cunha do; "A versatile synthesis to trisubstituted nitroalkenes via nitroaldol reaction: Synthesis of Baylis-Hillman type adducts", p-177-177. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013819161427