Inducing high exo selectivity in Diels-Alder reaction by dimethylborane substituent: a DFT study.

ABSTRACT: In this work, the role of Lewis acid-base (LAB) interaction on the stereoselectivity of the Diels-Alder (DA) reaction has been studied by DFT in gas and solution (dichloromethane) phases. The calculations were performed at the B3LYP/6-311G++ (d, p) level. Two different series of DA reactions were investigated: (1)-three mono-substituted cyclopentadienes + dimethyl(vinyl)borane; (2)-five α,β-unsaturated carbonyl compounds + cyclopenta-2,4-dien-1-yldimethylborane. The reacting diene and dienophile pairs were chosen to restrict LAB interaction to the exo reaction pathway. It was found that in some of the examined cases, the favorable LAB interaction is so strong that it can lead to a completely exo-selective DA reaction. Furthermore, a novel multistep synthetic method was hypothesized for pre

SUBMITTER: Taherinia D 

PROVIDER: S-EPMC9789069 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature