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Polymer-supportedN-benzyl- andN-benzhydryl-2-nitrobenzenesulfonamides as alternative to aldehyde linkers

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
45
Issue
22
Identifiers
DOI: 10.1016/j.tetlet.2004.04.003
Keywords
  • Solid-Phase Synthesis
  • Linker
  • 2-Nitrobenzenesulfonamides
  • Benzylamine

Abstract

Abstract Polymer-supported N-benzyl- and N-benzhydryl-2-nitrobenzenesulfonamides 1 were N-alkylated using three different routes: via Fukuyama reaction with alcohols, by N-alkylation with electrophiles, and by Michael addition reaction with α,β-unsaturated carbonyl compounds. The N-alkylated products were obtained in excellent purity and high yield. The 2-nitrobenzenesulfonyl (Nos) group was then cleaved to yield polymer-supported N-alkylated benzylamines and benzhydrylamines. N-alkylation of polymer-supported 2-nitrobenzenesulfonamide linkers 1 described herein represents an alternative route to reductive amination of aldehyde linkers.

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