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

Año: 2011 vol. 52 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.