Scavenge-ROMP-Filter: A Facile Strategy for Soluble Scavenging via Norbornenyl Tagging of Electrophilic Reagents

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1847-1849

  Moore, Joel D ^a   Harned, Andrew M ^a   Henle, Julia ^c   Flynn, Daniel L ^b   Hanson, Paul R ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b Neogenesis Pharmaceutical Inc   (United States)

^c UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

5 NORBORNENE 2 METHANOL; 5-NORBORNENE-2-METHANOL; ALCOHOL DERIVATIVE; AMINE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; METHANOL; NORBORNANE DERIVATIVE; POLYMER; SCAVENGER; SOLVENT;

ARTICLE; CATALYSIS; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ALCOHOLS; AMINES; CATALYSIS; FREE RADICAL SCAVENGERS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; METHANOL; NORBORNANES; POLYMERS; SOLVENTS;

EID: 0037198778     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0257880     Document Type: Article

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43. 1H NMR spectra of all crude products are available in the Supporting Information.
44. A comparative experiment of the reaction kinetics was made between the norbornene-based scavenger 1 and its comparable solid-phase equivalent, the hydroxymethyl resin (purchased from Irori). In this study, each alcohol scavenger (1.2 equiv) was tested for its reactivity toward the three electrophiles (1 equiv): p-toluenesulfonyl isocyanate, phenyl isocyanate, and benzoyl chloride. In the cases of p-TsNCO and the PhCOCl (0°C to rt), the norbornene-based scavenger reacted instantaneously with the electrophile, depleting its concentration to zero before any analysis could take place; in the PhNCO case, the tagged-scavenger reacted completely with the electrophile in 50 min (toluene, 100°C). The resin-bound scavenger reacted only slightly slower for the p-TsNCO (15 min); however, for PhCOCl and PhNCO, the resin-bound scavenger was dramatically slower (>2 h for PhCOCl and > 12 h for PhNCO).