On the discovery and development of tandem 1,4- and 1,2-addition of phosphites to 1-azadienes

Over the past 15 years we have developed a one-step protocol for the synthesis of 3-phosphonylated aminophosphonates from alpha,beta-unsaturated imines through tandem 1,4-1,2-phosphite addition. This account covers the initial development, mechanistic implications of using different phosphite nucleo...

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Hauptverfasser:	Van Waes, Frederik, Debrouwer, Wouter, Heugebaert, Thomas, Stevens, Christian
Format:	Artikel
Sprache:	eng
Schlagworte:	3-COMPONENT SYNTHESIS ALPHA ALPHA-AMINO PHOSPHONATES alpha_beta-unsaturated hydrazones alpha_beta-unsaturated imines alpha_beta-unsaturated oximes BETA-UNSATURATED IMINES BIOLOGICAL-ACTIVITY Chemistry diphosphonylation KABACHNIK-FIELDS REACTION METABOTROPIC GLUTAMATE-RECEPTOR MOLECULAR CHARACTERIZATION naphthyridines ONE-POT SYNTHESIS phenanthrolines Phosphonylation quinolines SIGNAL-TRANSDUCTION SOLVENT-FREE CONDITIONS tandem addition
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creator	Van Waes, Frederik Debrouwer, Wouter Heugebaert, Thomas Stevens, Christian
description	Over the past 15 years we have developed a one-step protocol for the synthesis of 3-phosphonylated aminophosphonates from alpha,beta-unsaturated imines through tandem 1,4-1,2-phosphite addition. This account covers the initial development, mechanistic implications of using different phosphite nucleophiles and the expansion towards oximes, hydrazones and unsaturated imines included in aromatic sextets, e. g. quinolines, phenanthrolines and napthyridines.
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source	Ghent University Academic Bibliography; DOAJ Directory of Open Access Journals; EZB-FREE-00999 freely available EZB journals
subjects	3-COMPONENT SYNTHESIS ALPHA ALPHA-AMINO PHOSPHONATES alpha_beta-unsaturated hydrazones alpha_beta-unsaturated imines alpha_beta-unsaturated oximes BETA-UNSATURATED IMINES BIOLOGICAL-ACTIVITY Chemistry diphosphonylation KABACHNIK-FIELDS REACTION METABOTROPIC GLUTAMATE-RECEPTOR MOLECULAR CHARACTERIZATION naphthyridines ONE-POT SYNTHESIS phenanthrolines Phosphonylation quinolines SIGNAL-TRANSDUCTION SOLVENT-FREE CONDITIONS tandem addition
title	On the discovery and development of tandem 1,4- and 1,2-addition of phosphites to 1-azadienes
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