Benzazetidines are highly strained and inherently unstable heterocycles. There are only few methodologies for assembling these compounds. Here, a protocol is presented to trap an elusive cyclic, four-membered hemiaminal structure. This method affords several benzazetidines in moderate to good yields (up to 81%), and it uses inexpensive materials and does not require catalysts based on transition metals. The high ring strain energy of these benzazetidine systems was estimated by density functional theory calculations to be about 32 kcal mor(-1). This synthesis can be applied also on gram scale with reaction yield essentially unchanged.

Salvio, R., Placidi, S., Sinibaldi, A., Di Sabato, A., Buscemi, D.c., Rossi, A., et al. (2019). Organocatalytic Synthesis of Benzazetidines by Trapping Hemiaminals with Protecting Groups. JOURNAL OF ORGANIC CHEMISTRY, 84(11), 7395-7404 [10.1021/acs.joc.9b01148].

Organocatalytic Synthesis of Benzazetidines by Trapping Hemiaminals with Protecting Groups

Salvio R.
;
2019-05-15

Abstract

Benzazetidines are highly strained and inherently unstable heterocycles. There are only few methodologies for assembling these compounds. Here, a protocol is presented to trap an elusive cyclic, four-membered hemiaminal structure. This method affords several benzazetidines in moderate to good yields (up to 81%), and it uses inexpensive materials and does not require catalysts based on transition metals. The high ring strain energy of these benzazetidine systems was estimated by density functional theory calculations to be about 32 kcal mor(-1). This synthesis can be applied also on gram scale with reaction yield essentially unchanged.
15-mag-2019
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/06 - CHIMICA ORGANICA
English
Con Impact Factor ISI
Salvio, R., Placidi, S., Sinibaldi, A., Di Sabato, A., Buscemi, D.c., Rossi, A., et al. (2019). Organocatalytic Synthesis of Benzazetidines by Trapping Hemiaminals with Protecting Groups. JOURNAL OF ORGANIC CHEMISTRY, 84(11), 7395-7404 [10.1021/acs.joc.9b01148].
Salvio, R; Placidi, S; Sinibaldi, A; Di Sabato, A; Buscemi, Dc; Rossi, A; Antenucci, A; Malkov, A; Bella, M
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/247668
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