Malkov_2019-04-26 manuscript_Salvio revised.pdf (519.43 kB)
Organocatalytic synthesis of benzazetidines by trapping hemiaminals with protecting groups
journal contribution
posted on 2019-06-03, 12:50 authored by Riccardo Salvio, Simone Placidi, Arianna Sinibaldi, Antonio Di Sabato, Dario C. Buscemi, Andrea Rossi, Achille Antenucci, Andrei MalkovAndrei Malkov, M. BellaBenzazetidines are highly strained and inherently unstable heterocycles. There are only few methodologies for assem-bling these compounds. Here, a protocol is presented to trap an elusive cyclic, 4-membered hemiaminal structure. This method affords several benzazetidine in moderate to good yields (up to 81%), 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 DFT calculations to be about 32 kcal mol-1. This synthesis can be applied also on gram scale with reac-tion yield essentially unchanged.
Funding
Authors wish to thank Sapienza Università di Roma for financial support through “Progetti di Ateneo” 2016 and 2017.
History
School
- Science
Department
- Chemistry
Published in
The Journal of Organic ChemistryVolume
84Issue
11Pages
7395-7404Citation
SALVIO, R. ... et al., 2019. Organocatalytic synthesis of benzazetidines by trapping hemiaminals with protecting groups. The Journal of Organic Chemistry, 84 (11), pp.7395-7404.Publisher
© American Chemical Society (ACS)Version
- AM (Accepted Manuscript)
Publisher statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.9b01148.Publication date
2019-05-15ISSN
0022-3263eISSN
1520-6904Publisher version
Language
- en