This article is cited in 4 papers

Communications

DFT and experimental study of triallylborane-mediated isomerization of α-allylated azaheterocycles

N. Yu. Kuznetsov^a, V. I. Malishev^abc, M. G. Medvedev^abd, Yu. N. Bubnov<sup>ab

a</sup> A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
^b N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^c Higher Chemical College of the Russian Academy of Sciences, D.I. Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation
^d National Research University Higher School of Economics (HSE University), Moscow, Russian Federation

Abstract: Triallylborane-mediated thermal trans/cis-isomerization of α-allylated azaheterocycles is a unique stereoselective transformation providing straightforward access to important heterocycles. The main experimental features of this process, namely, thermodynamically controlled isomer ratio, 1,3-allylic strain as a driving force and regioselectivity are quantitatively described by quantum chemical calculations at B3LYP/6-31+G(d,p)/PCM(DMSO) level of theory.

Language: English

DOI: 10.1016/j.mencom.2019.03.025

Bibliographic databases:

•