RT info:eu-repo/semantics/doctoralThesis
T1 Propargyl vinyl ethers : synthetic applications
A1 Méndez Abt, Gabriela
K1 Química orgánica
K1 Éteres
AB Microwave-assisted metal-free domino methodologies have been designed to transformpropargyl vinyl ethers (PVEs) I into products featuring structural diversity. Furthermore, theseprocesses have been designed to be fast, economical, bench-friendly (they do not requirespecial care with solvent and reaction atmospheres) and environmentally benign.It shown that the propargyl vinyl ether motives constitute a privileged group ofsmall size, structurally simple, readily available, and densely functionalized building blocks(they support a maximum of functional density on a minimum of skeletal connectivity). Thespatial clustering C3-O-C2 of a propargylic unit and a vinyl unit convert these structures inexcellent candidates to participate in the [3,3] propargylic sigmatropic rearrangement. This istherefore the key to the chemical reactivity encoded in these structures. With regard to thepropargyl Claisen rearrangement, as in any other [3,3]-sigmatropic rearrangement, it takesplace under thermodynamic control to generate the corresponding allenic esters II. Thisreaction is by all means irreversible toward the formation of the carbonyl compounds as theretro-Claisen rearrangement of allenic substrates has never been observed.The reactivity profile of these platforms has been therefore used to obtain collections ofcompounds with potential biological interest in a selective and efficient way, while developingnew domino methodologies.
PB Universidad de La Laguna, Servicio de Publicaciones
SN 978-84-15910-81-7
YR 2014
FD 2014
LK http://riull.ull.es/xmlui/handle/915/50
UL http://riull.ull.es/xmlui/handle/915/50
LA en
DS Repositorio institucional de la Universidad de La Laguna
RD 19-abr-2024