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Organocatalytic synthesis of benzazetidines by trapping hemiaminals with protecting groups

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journal contribution
posted on 03.06.2019 by Riccardo Salvio, Simone Placidi, Arianna Sinibaldi, Antonio Di Sabato, Dario C. Buscemi, Andrea Rossi, Achille Antenucci, Andrei Malkov, M. Bella
Benzazetidines 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 Chemistry

Volume

84

Issue

11

Pages

7395-7404

Citation

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

2019-05-15

ISSN

0022-3263

eISSN

1520-6904

Language

en

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