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Fragmentation of Carbohydrate Anomeric Alkoxyl Radicals. Synthesis of Organophosphorus Compounds Highly Functionalized

AuthorsRodríguez Morales, María S. ; Hernández-Guerra, Daniel ; Suárez, Ernesto
Issue Date1-Oct-2014
CitationWG4/WG1 Meeting COST Action CM1201: Biomimetic Radical Chemistry (2014)
AbstractThe alkoxyl radical fragmentation (ARF) reaction of carbohydrate anomeric alcohols with hypervalent iodine reagents in the presence of iodine has been described by this laboratory. The synthesis of chiral vinylphosphonate and vinylphosphine oxide carbohydrate derivatives has been developed using this protocol. The synthetic sequence proceeded via β‐iodophosphonate and β‐iodophosphine oxide intermediates, which may be interesting synthons for the introduction of phosphorus into complex organic molecules (Scheme 1). These vinylphosphonates could be easily transformed into α‐methylene‐γ‐phostones (O–P‐ cyclization) and β‐aminophosphonates, isosteres of biologically active α‐methylene‐γ‐lactones and β‐ amino acids, respectively. β‐Iodophosphine oxides were easily converted into cyclic 1,4‐anhydro‐2‐ deoxy‐2‐phosphoryl‐alditol derivatives (O–C‐cyclization). We have also used these conjugated vinylphosphorus compounds as radical acceptors in photostimulated alkyl radical addition reactions (Scheme 2).Using the ARF reaction as key step, we have developed a new general methodology for the synthesis of phostones and phostines (Scheme 3). The organophosphorus were obtained by Arbuzov reaction hat finally produced 1‐phospha‐sugars in good yields. The talk will focus on this research and recent advances on the synthesis of new organophosphorus compunds.
DescriptionTrabajo presentado en el WG4/WG1 Meeting COST Action CM1201: Biomimetic Radical Chemistry, celebrado en el Puerto de la Cruz (Tenerife) del 1 al 3 de octubre de 2014.
Appears in Collections:(IPNA) Comunicaciones congresos
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