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

SAROTTI, ARIEL M.; SUÁREZ, ALEJANDRA G.; SPANEVELLO, ROLANDO A.

TETRAHEDRON LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; 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.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.