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

Sarotti, Ariel Marcelo; Suarez, Alejandra Graciela; Spanevello, Rolando Angel

info:eu-repo/semantics/article

Fecha

2011-06

Registro en:

Sarotti, Ariel Marcelo; Suarez, Alejandra Graciela; Spanevello, Rolando Angel; DFT calculations induced a regiochemical outcome revision of the Diels-Alder reaction between levoglucosenone and isoprene; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 52; 24; 6-2011; 3116-3119

0040-4039

http://hdl.handle.net/11336/127148

CONICET Digital

CONICET

https://repositorioslatinoamericanos.uchile.cl/handle/2250/4396124

Autor

Sarotti, Ariel Marcelo

Suarez, Alejandra Graciela

Spanevello, Rolando Angel

Institución

Consejo Nacional de Investigaciones Científicas y Tecnológicas (Argentina)

Resumen

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

Materias

DFT

DIELS-ALDER

LEVOGLUCOSENONE

REGIOCHEMISTRY

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