1-Amino-1-hydroxymethylcyclobutane Derivatives via Intramolecular Amination of Nonclassical Cyclopropylmethyl Cation
Chemistry of Heterocyclic Compounds 2017
Marija Skvorcova, Liene Grigorjeva, Aigars Jirgensons

Bis(trichloroacetimidoyloxymethyl)cyclopropa nes provide intramolecular amination products of intermed iate cyclobutyl or cyclopr opyl-methyl carbenium ion when exposed to Lewis acid catalyst or thermal ionization. The ratio of the two amination products of cyclobutyl carbenium ion depends primarily on the substituent at the alkoxymet hyl group of the substrate and can be altered by the solvent used and the ionization conditions. An oxazoline deri vative forms as the major amination produc t in the case of unsubstituted bis(trichl o-roacetimidoyloxymethyl)cyclopropane or if the substrate contains isopropyl or alkoxymethyl substituents. The amination of cyclobutyl carbenium ion formed in situ proceeds with high diastereoselectivity leading to exclusive formation of trans- cyclobutane derivatives. The latter can be transformed to N-Boc-protected cyclobutane-based amino alcohols in high yields.


Atslēgas vārdi
amino alcohol, carbenium ion, cyclobutane, 5-oxa-7-azaspiro[2.5]oct-6-ene, 5-oxa-7-azaspiro[3.4]oct-5-ene, 1,3-oxazine, oxazoline, trichloroacetimidate, Lewis acid.
DOI
10.1007/s10593-017-2162-1
Hipersaite
http://hgs.osi.lv/index.php/hgs/article/view/3996

Skvorcova, M., Grigorjeva, L., Jirgensons, A. 1-Amino-1-hydroxymethylcyclobutane Derivatives via Intramolecular Amination of Nonclassical Cyclopropylmethyl Cation. Chemistry of Heterocyclic Compounds, 2017, Vol.53, No.9, 989.-996.lpp. ISSN 0009-3122. e-ISSN 1573-8353. Pieejams: doi:10.1007/s10593-017-2162-1

Publikācijas valoda
English (en)
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