Vinyl sulfones in solid-phase synthesis: Preparation of 4,5,6,7-tetrahydroisoindole derivatives

W. C. Cheng, M. M. Olmstead, M. J. Kurth

Research output: Contribution to journalArticle

38 Scopus citations

Abstract

The preparation of functionalized 4,5,6,7-tetrahydroisoindole via a traceless solid-phase sulfone linker strategy is described. Thermolytic extrusion of SO2 from polymer-bound 3-(phenylsulfonyl)-3-sulfolene (7) generated polymer-bound 2-(phenylsulfonyl)-1,3-butadiene (9) in situ which underwent Diels-Alder cycloaddition with various dienophiles to furnish vinyl sulfone resins 10-14. To complete a traceless linker cleavage strategy, (p-tolysulfonyl)methyl isocyanide or ethyl isocyanoacetate was employed to react with the vinyl sulfone moiety to liberate functionalized 4,5,6,7-tetrahydroisoindole products from the resin. Using this chemistry, nine tetrahydroisoindole derivatives (6, 15-22) were prepared in 32-41% overall yields from polystyrene/divinylbenzene sulfinate 1.

Original languageEnglish (US)
Pages (from-to)5528-5533
Number of pages6
JournalJournal of Organic Chemistry
Volume66
Issue number16
DOIs
StatePublished - Aug 10 2001

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Vinyl sulfones in solid-phase synthesis: Preparation of 4,5,6,7-tetrahydroisoindole derivatives'. Together they form a unique fingerprint.

  • Cite this