Selective synthesis of N-protected exo-spiro[oxirane-3,2′-tropanes]

Aleksandr Mandzhulo; Iryna Vashchenko; Andrii Gerasov; Mykhaylo Vovk; Eduard Rusanov; Volodymyr Fetyukhin; Oleg Lukin; Alexander Shivanyuk

doi:10.1039/C9QO00377K

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Selective synthesis of N-protected exo-spiro[oxirane-3,2′-tropanes]†

Aleksandr Mandzhulo,^ab Iryna Vashchenko,^a Andrii Gerasov,^a Mykhaylo Vovk,^b Eduard Rusanov,^b Volodymyr Fetyukhin,^a Oleg Lukin^a and Alexander Shivanyuk

*^ac

Author affiliations

* Corresponding authors

^a Life Chemicals Inc., Murmanska Str. 5, Kyiv, Ukraine
E-mail: A.Shivanyuk@lifechemicals.com

^b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Str 5, Kyiv, Ukraine

^c The Institute of High Technologies, Taras Shevchenko National University of Kyiv, 4 Glushkov st. 5, Kyiv, Ukraine

Abstract

N-Cbz- and N-Boc-protected exo-spiro[oxirane-3,2′-tropanes] were obtained in 62–75% yield via either epoxidation or hydroxybromination/dehydrobromination of the corresponding alkenes. Deprotection of the Cbz-exo-epoxide afforded the corresponding tropane containing an exo-oxirane fragment and a secondary amino group.

This article is part of the themed collection: In celebration of Julius Rebek’s 75th Birthday

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DOI: https://doi.org/10.1039/C9QO00377K
Article type: Research Article
Submitted: 15 Mrz 2019
Accepted: 04 Apr 2019
First published: 11 Apr 2019

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Org. Chem. Front., 2019,6, 1692-1697

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Selective synthesis of N-protected exo-spiro[oxirane-3,2′-tropanes]

A. Mandzhulo, I. Vashchenko, A. Gerasov, M. Vovk, E. Rusanov, V. Fetyukhin, O. Lukin and A. Shivanyuk, Org. Chem. Front., 2019, 6, 1692 DOI: 10.1039/C9QO00377K

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Organic Chemistry Frontiers

Selective synthesis of N-protected exo-spiro[oxirane-3,2′-tropanes]†

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Selective synthesis of N-protected exo-spiro[oxirane-3,2′-tropanes]

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