V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, O. M. Nefedov, “Synthesis of vicinal (alkylamino)alkynylcyclopropanes from geminal alkynyl(chloro)cyclopropanes”, Mendeleev Commun., 2021, Volume 31, Issue 5,Pages <nobr>654

This article is cited in 4 papers

Communications

Synthesis of vicinal (alkylamino)alkynylcyclopropanes from geminal alkynyl(chloro)cyclopropanes

V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, O. M. Nefedov

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: New N-Boc-alkyl(2-alkynylcyclopropyl)amines were synthesized from 1-alkynyl-1-chlorocyclopropanes and N-Boc- alkylamines under the action of Bu^tOK in DMSO, the intermediates having been the corresponding conjugated alkynylcyclopropenes. The Boc-derivatives can be converted into free secondary 2-alkynylcyclopropylamines, as well as β-lithiated with subsequent alkylation.

Keywords: alkynyl(chloro)cyclopropanes, 1-amino-2-alkynylcyclopropanes, cyclopropylamines, cyclopropenes, protecting groups, directing groups, lithiation, alkylation, stereoselectivity.

Language: English

DOI: 10.1016/j.mencom.2021.09.020

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