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Synthesis of azabicyclo[n.1.0]alkane-derived bifunctional building blocks via the Corey–Chaykovsky cyclopropanation |
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| Authors: | Dmytro V Yarmoliuk Dmytro Serhiichuk Vladyslav Smyrnov Andriy V Tymtsunik Oleksandr V Hryshchuk Yuliya Kuchkovska Oleksandr O Grygorenko |
| Institution: | 1. Enamine Ltd. (www.enamine.net), Chervonotkatska Street 78, Kyiv 02094, Ukraine;2. National Taras Shevchenko University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine;3. National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”, Prospect Peremogy 37, Kyiv 03056, Ukraine |
| Abstract: | An efficient approach towards the synthesis of monoprotected azabicyclo5.1.0]octane-derived conformationally restricted γ-amino acids and diamines is reported. Optimization of the conditions for the key Corey–Chaykovsky reaction allowed the construction of two isomeric methanoazepane frameworks on a multigram scale in 55–65% yield. Additionally, the developed approach was used in the three-step synthesis of 3,4-methano-β-proline and its diamine derivatives. |
| Keywords: | Amino acids Bicyclic compounds Azepane Cyclopropane Pyrrolidine Diamines |
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