Functionalized cross-linked poly(vinyl alcohol) resins as reaction scavengers and as supports for solid-phase organic synthesis

Zheng Wang, Juntao Luo, X. X. Zhu, Shujuan Jin, Mirosław J. Tomaszewski

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

New hydrophilic poly(vinyl alcohol) (PVA-OH) resins were prepared by an inverse suspension polymerization using epichlorohydrin as a cross-linker. These novel resins swell in a variety of solvents commonly used in solid-phase organic synthesis, such as dicholomethane, dioxane, methanol, tetrahydrofuran, and dimethyl-formamide. In addition, PVA-OH shows excellent swelling in water. The cross-linked PVA-OH beads were functionalized with an aldehyde group and were tested as scavengers for primary amines in three different reactions: amide bond formation, reductive amination reaction, and urea formation. With 1-2 equiv of the PVA aldehyde resin, all the excess primary amines were successfully scavenged. The utility of PVA-OH resins as solid supports in mono- and dipeptide synthesis was also investigated using symmetrical anhydride and MSNT/MeIm (2,4,6-mesitylenesulfonyl-3-nitro-1,2,4-triazolide in the presence of 1-methylimidazol) methods.

Original languageEnglish (US)
Pages (from-to)961-966
Number of pages6
JournalJournal of Combinatorial Chemistry
Volume6
Issue number6
DOIs
StatePublished - Nov 2004
Externally publishedYes

Fingerprint

Synthetic Chemistry Techniques
Solid-Phase Synthesis Techniques
Alcohol
Resins
Alcohols
Synthesis
Aldehydes
Amines
Epichlorohydrin
Amination
Anhydrides
Swelling
Dipeptides
Polymerization
Dimethylformamide
Amides
Methanol
Excess
Urea
Suspensions

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Discrete Mathematics and Combinatorics

Cite this

Functionalized cross-linked poly(vinyl alcohol) resins as reaction scavengers and as supports for solid-phase organic synthesis. / Wang, Zheng; Luo, Juntao; Zhu, X. X.; Jin, Shujuan; Tomaszewski, Mirosław J.

In: Journal of Combinatorial Chemistry, Vol. 6, No. 6, 11.2004, p. 961-966.

Research output: Contribution to journalArticle

Wang, Zheng ; Luo, Juntao ; Zhu, X. X. ; Jin, Shujuan ; Tomaszewski, Mirosław J. / Functionalized cross-linked poly(vinyl alcohol) resins as reaction scavengers and as supports for solid-phase organic synthesis. In: Journal of Combinatorial Chemistry. 2004 ; Vol. 6, No. 6. pp. 961-966.
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