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

SAROTTI, A. M.; SUÁREZ, A. G.; SPANEVELLO, R. A.

TETRAHEDRON LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2011 vol. 2011 p. 3116 - 3119

0040-4039

An appealing inversion in the regiochemical outcome of Diels–Alder reactions between levoglucosenone (1) and its a-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.