DFT calculations induced a regiochemical outcome revision of the Diels-Alder reaction between levoglucosenone and isoprene

An appealing inversion in the regiochemical outcome of Die Is-Alder reactions between levoglucosenone (1) and its alpha-bromo derivative (5) with isoprene (2) was studied computationally. Based on different DFT calculations we concluded that both reactions should display the same regioselectivity. This result was further validated experimentally. (C) 2011 Elsevier Ltd. All rights reserved.