Stereospecificity of a New Reaction of L-Ascorbic Acid with Cis and Trans Olefinic 1,4-Dicarbonyl Compounds

Gabor Fodor, Kawporn Sussangkarn, Hansie Mathelier, Kang Fang, Regina Arnold, Judith Flippen-Anderson, Isabella Karle

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18 Citations (Scopus)

Abstract

The Michael-type addition of the ascorbate carbanion upon α,β-unsaturated carbonyl compounds is compared with the aldol-like addition of the same carbanion to the related 1,4-dioxo olefins. In contrast to the behavior of maleic aldehyde and 3-acetylacrolein that leads to 4, the primary aldol adduct of 1 to fumaric aldehyde is stabilized by internal Michael addition as a tetracyclic lactone–cycloketal hemiacetal (6). This structure is based on 13C NMR, 1H NMR, and ultimately X-ray crystallographic work.

Original languageEnglish
Pages (from-to)3148-3150
Number of pages3
JournalJournal of Organic Chemistry
Volume51
Issue number16
DOIs
Publication statusPublished - 1986 Jan 1

ASJC Scopus subject areas

  • Organic Chemistry

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    Fodor, G., Sussangkarn, K., Mathelier, H., Fang, K., Arnold, R., Flippen-Anderson, J., & Karle, I. (1986). Stereospecificity of a New Reaction of L-Ascorbic Acid with Cis and Trans Olefinic 1,4-Dicarbonyl Compounds. Journal of Organic Chemistry, 51(16), 3148-3150. https://doi.org/10.1021/jo00366a013