Quantum Chemical-Guided Steglich Rearrangement of Azlactones and Isoxazolones.
Pedro P De CastroJuliana A Dos SantosMarcelo M De SiqueiraGabriel M F BatistaHélio F Dos SantosGiovanni Wilson AmarantePublished in: The Journal of organic chemistry (2019)
The theoretical-guided evaluation of the Steglich rearrangement of azlactones and isoxazolones allowed the determination of the reactivity patterns in these heterocycles, including the factors that drive the regioselectivity toward both possible sites. These results allowed the first experimental report on the regioselective Steglich rearrangement of isoxazolones, affording the nitrogen- or carbon-acyloxy adducts.