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

Research output: Contribution to journalArticle

28 Scopus citations

Abstract

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 (US)
Pages (from-to)5089-5097
Number of pages9
JournalJournal of Organic Chemistry
Volume65
Issue number17
DOIs
StatePublished - Aug 25 2000

ASJC Scopus subject areas

  • Organic Chemistry

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    Avalos, M., Babiano, R., Cintas, P., Clemente, F. R., Gordillo, R., Jiménez, J. L., Palacios, J. C., & Raithby, P. R. (2000). Diastereoselective cycloadditions of 1,3-thiazolium-4-olates with chiral 1,2-diaza-1,3-butadienes. Journal of Organic Chemistry, 65(17), 5089-5097. https://doi.org/10.1021/jo991841v