Jump to main content
Jump to site search

Issue 6, 2004
Previous Article Next Article

Ring-closing metathesis: development of a cyclisation–cleavage strategy for the solid-phase synthesis of cyclic sulfonamides

Author affiliations

Abstract

A series of novel 7-membered cyclic sulfonamides have been synthesised using a solid-phase cyclisation–cleavage RCM strategy. Model solution studies indicated the sulfonamides were suitable substrates for RCM using the Grubbs' catalyst 2. Starting from either 2-carboxyethyl polystyrene (21) or Merrifield resin, various seven-membered sulfonamides were prepared in good to excellent yields at low catalyst loadings (2.5–5 mol%) using a flexible spacer between the polymer and the substrate. In addition, a novel double-armed linker was shown to allow efficient RCM cleavage of sulfonamides with as little as 1 mol% of the ruthenium alkylidene complex 2.

Graphical abstract: Ring-closing metathesis: development of a cyclisation–cleavage strategy for the solid-phase synthesis of cyclic sulfonamides

Back to tab navigation

Publication details

The article was received on 30 Oct 2003, accepted on 05 Jan 2004 and first published on 16 Feb 2004


Article type: Paper
DOI: 10.1039/B313686H
Citation: Org. Biomol. Chem., 2004,2, 835-844
  •   Request permissions

    Ring-closing metathesis: development of a cyclisation–cleavage strategy for the solid-phase synthesis of cyclic sulfonamides

    J. Moriggi, L. J. Brown, J. L. Castro and R. C. D. Brown, Org. Biomol. Chem., 2004, 2, 835
    DOI: 10.1039/B313686H

Search articles by author

Spotlight

Advertisements