Intra- and intermolecular 1,3-dipolar cycloaddition of sugar ketonitrones with mono-, di-, and trisubstituted dipolarophiles

Susana Torrente, Beatriz Noya, Vicenç Branchadell, Ricardo Alonso

Research output: Contribution to journalArticleResearchpeer-review

33 Citations (Scopus)

Abstract

The 1,3-dipolar cycloaddition of sugar ketonitrones is a useful synthetic procedure to build up nitrogenated quaternary centers in terms of scope (substrate, dipolarophile, inter- and intramolecular versions), yield, and regio- and stereoselectivity. The hybrid ONIOM (B3LYP/6-31G(d): AM1) theoretical method followed by single-point energy calculations at the B3LYP/6-31G(d) level adequately perform to model this cycloaddition for the relatively large ketosugar precursors commonly used.
Original languageEnglish
Pages (from-to)4772-4783
JournalJournal of Organic Chemistry
Volume68
Issue number12
DOIs
Publication statusPublished - 13 Jun 2003

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