Issue 10, 2019

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

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]

Supplementary files

Article information

Article type
Research Article
Submitted
15 mar 2019
Accepted
04 apr 2019
First published
11 apr 2019

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

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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