[2+2]-Photocycloaddition of N‑Benzylmaleimide to Alkenes As an Approach to Functional 3‑Azabicyclo[3.2.0]heptanes

[2+2]-Photocycloaddition of N‑Benzylmaleimide to Alkenes As an Approach to Functional 3‑Azabicyclo[3.2.0]heptanes

A one-step synthesis of functionalized 3-azabicyclo[3.2.0]­heptanes by [2+2]-photochemical intermolecular cycloaddition of N-benzylmaleimide to alkenes was elaborated. The obtained compounds were easily transformed into the bi- and tricyclic analogues of piperidine, morpholine, piperazine, and GABA,...

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Veröffentlicht in:Journal of organic chemistry 2018-06, Vol.83 (12), p.6275-6289
Hauptverfasser: Skalenko, Yevhen A, Druzhenko, Tetiana V, Denisenko, Aleksandr V, Samoilenko, Maryna V, Dacenko, Oleksandr P, Trofymchuk, Serhii A, Grygorenko, Oleksandr O, Tolmachev, Andrey A, Mykhailiuk, Pavel K
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Sprache:eng
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Zusammenfassung:A one-step synthesis of functionalized 3-azabicyclo[3.2.0]­heptanes by [2+2]-photochemical intermolecular cycloaddition of N-benzylmaleimide to alkenes was elaborated. The obtained compounds were easily transformed into the bi- and tricyclic analogues of piperidine, morpholine, piperazine, and GABA, which are advanced building blocks for drug discovery.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00077