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

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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.

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

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Publication details

The article was received on 15 Mar 2019, accepted on 04 Apr 2019 and first published on 11 Apr 2019


Article type: Research Article
DOI: 10.1039/C9QO00377K
Citation: Org. Chem. Front., 2019, Advance Article

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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, Advance Article , DOI: 10.1039/C9QO00377K

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