caa a22 4500 60551271X CHVBK 20210128100657.0 cr unu---uuuuu 210128e20150401xx s 000 0 eng 10.1007/s00894-015-2636-y doi (NATIONALLICENCE)springer-10.1007/s00894-015-2636-y Theoretical study of the mechanism of highly diastereoselective formation of a strained 3-azabicyclo[3.2.0]heptane derivative [Elektronische Daten] [Maryam Nemati, Nematollah Arshadi] The mechanism of multicomponent reactions, especially stereoselective ones is of special importance in organic synthesis. The mechanism of diastereoselective formation of a highly strained 3-azabicyclo[3.2.0]heptane derivative through a catalyst-free multistep reaction is studied by DFT calculations in solution phase. The calculations on the two proposed mechanisms (pathways A and B) showed that the iminium ion, the relatively high energy species is not the approprite reaction intermediate. On the other hand, the lower activation energy of pathway B, as compared to that of pathway A, makes it as the preferred mechanism. The high stereoselectivity of the stepwise reaction may be attributed to the fact that the rate limiting and stereodifferentiating steps are the same. These findings may also account the formation of by-product in the experimental observations. Graphical Abstract Finding a more reasonable explanation for highly diastereoselective formation of a strained 3-azabicyclo[3.2.0]heptane derivative Springer-Verlag Berlin Heidelberg, 2015 Density functional theory (DFT) calculations nationallicence Diastereoslectivity nationallicence Highly strained bicyclic compounds nationallicence Iminium ion nationallicence Multicomponent reactions' mechanism nationallicence Nemati Maryam Department of Chemistry, Faculty of Sciences, University of Zanjan, Zanjan, Iran aut Arshadi Nematollah Department of Chemistry, Faculty of Sciences, University of Zanjan, Zanjan, Iran aut Journal of Molecular Modeling Springer Berlin Heidelberg 21/4(2015-04-01), 1-10 1610-2940 21:4<1 2015 21 894 https://doi.org/10.1007/s00894-015-2636-y text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00894-015-2636-y text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Nemati Maryam Department of Chemistry, Faculty of Sciences, University of Zanjan, Zanjan, Iran aut NATIONALLICENCE 700 1- Arshadi Nematollah Department of Chemistry, Faculty of Sciences, University of Zanjan, Zanjan, Iran aut NATIONALLICENCE 773 0- Journal of Molecular Modeling Springer Berlin Heidelberg 21/4(2015-04-01), 1-10 1610-2940 21:4<1 2015 21 894