An intramolecular [2 + 2] photocycloaddition approach to conformationally restricted bis-pyrrolidines

Diego A. Fort, Thomas J. Woltering, André M. Alker, Thorsten Bach

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

With N-Boc-protected 4-(allylaminomethyl)-2(5H)furanones as starting materials, a photochemical approach is presented to give 3,9-diazatricyclo[5.3. 0.01,5]decanes as conformationally restricted bis-pyrrolidines. The products are orthogonally protected at the two nitrogen atoms and exhibit, depending on the substitution pattern at positions C5, C6, and C7, latent C 2 symmetry. When the furanones had a phenyl group at the 3-position (X3), alternative photochemical pathways were observed.

Original languageEnglish
Pages (from-to)7152-7161
Number of pages10
JournalJournal of Organic Chemistry
Volume79
Issue number15
DOIs
StatePublished - Aug 2014

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