Show simple item record

dc.contributor.advisorTorres, Wildeliz
dc.contributor.authorCorrea, Fernando
dc.date.accessioned2019-07-01T16:51:51Z
dc.date.available2019-07-01T16:51:51Z
dc.date.issued2019-05-15
dc.identifier.urihttps://hdl.handle.net/20.500.11801/2477
dc.description.abstractBecause of its unique reactivity profile and synthetic utility, epoxides have captivated and attracted the organic chemistry community since their discovery. They are valuable precursors of many bioactive natural and unnatural compounds and there is an incessant interest in the development of green methods that give access to these scaffolds efficiently. Herein, we report an unprecedented Darzens reaction that uses an α-mesyloxyketone as substrate for the synthesis of 10 representative examples in moderate to good yield (12-71%). This reaction was then applied in tandem to a known gold-catalyzed alkyne oxidation that made possible the direct conversion of terminal alkynes to α,β-epoxyketones albeit in moderate yields (15-22%). Even though further optimization is needed for the tandem process this method allows for a dramatic and rapid increase in substrate complexity from simple and affordable starting materials.en_US
dc.description.abstractDesde su descubrimiento, debido a su reactividad peculiar y utilidad sintética, los epóxidos han generado gran interés en el mundo de la química orgánica. Son precursores de muchos compuestos biológicamente activos. Por ende, hay un interés incesante en desarrollar métodos benignos que permitan acceso a dichas estructuras de manera eficiente. Aquí reportamos una reacción Darzens sin precedentes que utiliza una α-mesiloxicetona como sustrato y que permitió la síntesis de 10 ejemplos representativos en rendimientos moderados a altos (12-71%). Dicha reacción fue aplicada simultáneamente a un proceso de oxidación de alquinos terminales que permitió la conversión directa a α,β-epoxicetonas, aunque en rendimientos moderados (15-22%). Aunque es necesario optimizar las condiciones de este proceso, el mismo hace que sea posible aumentar rápidamente la complejidad de sustratos simples y asequibles.en_US
dc.description.sponsorshipPuerto Rico Science Trust: Small Innovation Granten_US
dc.language.isoenen_US
dc.subjectDarzensen_US
dc.subjectEpoxidesen_US
dc.subjectTandemen_US
dc.subjectTerminal alkyneen_US
dc.subjectSynthesisen_US
dc.subject.lcshEpoxy compoundsen_US
dc.subject.lcshChemistry, Organicen_US
dc.subject.lcshOrganic compounds -- Synthesisen_US
dc.subject.lcshDarzens reactionen_US
dc.subject.lcshAlkynesen_US
dc.titleA new tandem strategy for the synthesis of α,β-epoxyketones from terminal alkynesen_US
dc.typeThesisen_US
dc.rights.licenseAll rights reserved
dc.rights.holder(c) 2019 Fernando Correa Delgadoen_US
dc.contributor.committeeMorell, Luis
dc.contributor.committeeGuzmán, Aikomarí
dc.contributor.committeeMeléndez, Enrique
dc.contributor.representativePérez, Fernando
thesis.degree.levelM.S.en_US
thesis.degree.disciplineChemistryen_US
dc.contributor.collegeCollege of Arts and Sciences - Sciencesen_US
dc.contributor.departmentDepartment of Chemistryen_US
dc.description.graduationSemesterSpringen_US
dc.description.graduationYear2019en_US


Files in this item

Thumbnail

This item appears in the following Collection(s)

  • Theses & Dissertations
    Items included under this collection are theses, dissertations, and project reports submitted as a requirement for completing a degree at UPR-Mayagüez.

Show simple item record

All rights reserved
Except where otherwise noted, this item's license is described as All Rights Reserved