About: Oxidative tandem alkoxide conjugate addition to nitroalkenes/radical 5-exo cyclizations-a versatile synthesis of functionalized 3-nitrotetrahydrofurans

Facets (new session)
Description
Metadata
Settings
- owl:sameAs
- Inference Rule:

About: Oxidative tandem alkoxide conjugate addition to nitroalkenes/radical 5-exo cyclizations-a versatile synthesis of functionalized 3-nitrotetrahydrofurans Goto Sponge NotDistinct Permalink

An Entity of Type : http://linked.opendata.cz/ontology/domain/vavai/Vysledek, within Data Space : linked.opendata.cz associated with source document(s)

Attributes	Values
rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Structurally diverse functionalized 4-(1-haloalkyl)-3-nitrotetrahydrofurans were conveniently obtained in moderate to good yield and moderate to very good diastereoselectivity by an oxidative tandem process consisting of conjugate addition reaction of lithium allyloxides to nitroalkenes followed by SET oxidation of the resulting nitronates. This triggers a radical cyclization; ligand transfer from the oxidant provides the products. The influence of the counter ion of the initial alkoxide and intermediate nitronate, the solvent and additives on the outcome of the tandem process was investigated. Optimal conditions for the tandem reactions consist of using butyllithium as the base for deprotonation in DME as the solvent. Cupric halides proved to be the SET oxidants of choice in the tandem reactions. A stereochemical model for the radical cyclization and ligand transfer steps is proposed. Structurally diverse functionalized 4-(1-haloalkyl)-3-nitrotetrahydrofurans were conveniently obtained in moderate to good yield and moderate to very good diastereoselectivity by an oxidative tandem process consisting of conjugate addition reaction of lithium allyloxides to nitroalkenes followed by SET oxidation of the resulting nitronates. This triggers a radical cyclization; ligand transfer from the oxidant provides the products. The influence of the counter ion of the initial alkoxide and intermediate nitronate, the solvent and additives on the outcome of the tandem process was investigated. Optimal conditions for the tandem reactions consist of using butyllithium as the base for deprotonation in DME as the solvent. Cupric halides proved to be the SET oxidants of choice in the tandem reactions. A stereochemical model for the radical cyclization and ligand transfer steps is proposed. (en)
Title	Oxidative tandem alkoxide conjugate addition to nitroalkenes/radical 5-exo cyclizations-a versatile synthesis of functionalized 3-nitrotetrahydrofurans Oxidative tandem alkoxide conjugate addition to nitroalkenes/radical 5-exo cyclizations-a versatile synthesis of functionalized 3-nitrotetrahydrofurans (en)
skos:prefLabel	Oxidative tandem alkoxide conjugate addition to nitroalkenes/radical 5-exo cyclizations-a versatile synthesis of functionalized 3-nitrotetrahydrofurans Oxidative tandem alkoxide conjugate addition to nitroalkenes/radical 5-exo cyclizations-a versatile synthesis of functionalized 3-nitrotetrahydrofurans (en)
skos:notation	RIV/61388963:_____/12:00376850!RIV13-AV0-61388963
http://linked.open...avai/riv/aktivita	Z
http://linked.open...avai/riv/aktivity	Z(AV0Z40550506)
http://linked.open...iv/cisloPeriodika	5
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Jahn, Ullrich
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	157555
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/12:00376850
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	electron transfer; tandem reaction; tetrahydrofurans; oxidation; radicals (en)
http://linked.open.../riv/klicoveSlovo	electron transfer oxidation radicals tandem reaction tetrahydrofurans
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[BE3E19A15551]
http://linked.open...i/riv/nazevZdroje	Tetrahedron
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	68
http://linked.open...iv/tvurceVysledku	Jahn, Ullrich Jones, P. G. Rudakov, D.
http://linked.open...ain/vavai/riv/wos	000299759000025
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství
issn	0040-4020
number of pages	19 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.tet.2011.12.010

Faceted Search & Find service v1.16.118 as of Jun 21 2024

Alternative Linked Data Documents: ODE Content Formats:

RDF

ODATA

Microdata

About

OpenLink Virtuoso version 07.20.3240 as of Jun 21 2024, on Linux (x86_64-pc-linux-gnu), Single-Server Edition (126 GB total memory, 48 GB memory in use)
Data on this page belongs to its respective rights holders.
Virtuoso Faceted Browser Copyright © 2009-2024 OpenLink Software