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The synthesis of a 2-azabicyclo[3.1.0]hexane by rearrangement of a spirocyclic epoxide |
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| Authors: | Mykhailo I. Adamovskyi Oleksiy S. Artamonov Andriy V. Tymtsunik Oleksandr O. Grygorenko |
| Affiliation: | 1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, Kyiv 02660, Ukraine;2. National Taras Shevchenko University of Kyiv, Volodymyrska Street, 64, Kyiv 01601, Ukraine |
| Abstract: | An unusual rearrangement of a 1-oxa-6-azaspiro[2.5]octane derivative giving access to novel 5-substituted 2-azabicyclo[3.1.0]hexanes is described. The synthetic application of the reaction is demonstrated by the synthesis of N-Boc-2,3-methano-β-proline. The amino acid was prepared through a three-step synthesis from easily available reagents in an overall yield of 15%. |
| Keywords: | VWXMXVVMJQHITP-UHFFFAOYSA-N ULSBMKGFFFMGOI-UHFFFAOYSA-N ILVWYZYLTRYTDX-UHFFFAOYSA-N |
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