Diastereoselective cycloadditions of 1,3-thiazolium-4-olates with chiral 1,2-diaza-1,3-butadienes

Martín Avalos, Reyes Babiano, Pedro Cintas, Fernando R. Clemente, Ruth Gordillo, José L. Jiménez, Juan C. Palacios, Paul R. Raithby

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34 Citations (SciVal)


A series of 2-(N-methyl)benzylamino-1,3-thiazolium-4-olates (2-aminothioisomunchnones) react with chiral 1,2-diaza-1,3-butadienes derived from carbohydrates to afford a diastereomeric mixture of (4R,5S)- and (4R,5R)-4,5-dihydrothiophenes. These substrate-controlled cycloadditions are chemoselective, regiospecific, and proceed with a high facial diastereoselection. A theoretical rationale at semiempirical level does justify the stereochemical outcome observed in the experiments.

Original languageEnglish
Pages (from-to)5089-5097
Number of pages9
JournalJournal of Organic Chemistry
Issue number17
Publication statusPublished - 25 Aug 2000

ASJC Scopus subject areas

  • Organic Chemistry


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