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

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

Journal

Mendeleev Communications
ISSN: 1364-551X , E-ISSN: 0959-9436

Output data

Year: 2019, Volume: 29, Number: 2, Pages: 190-193 Pages count : 4 DOI: 10.1016/j.mencom.2019.03.025

Authors

Kuznetsov Nikolai Yu. ¹ , Malishev Vadim I. ^1,2,3 , Medvedev Michael G. ^1,2,4 , Bubnov Yurii N. ^1,2

Affiliations

1	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
3	Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russian Federation
4	National Research University Higher School of Economics, 101000 Moscow, Russian Federation

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.

Kuznetsov N.Y. , Malishev V.I. , Medvedev M.G. , Bubnov Y.N.
DFT and experimental study of triallylborane-mediated isomerization of α-allylated azaheterocycles
Mendeleev Communications. 2019. V.29. N2. P.190-193. DOI: 10.1016/j.mencom.2019.03.025 WOS Scopus OpenAlex

≡ Web of science:	WOS:000467509600025
≡ Scopus:	2-s2.0-85064315016
≡ OpenAlex:	W2936585168