TY - JOUR
T1 - Stereospecificity of a New Reaction of L-Ascorbic Acid with Cis and Trans Olefinic 1,4-Dicarbonyl Compounds
AU - Fodor, Gabor
AU - Sussangkarn, Kawporn
AU - Mathelier, Hansie
AU - Fang, Kang
AU - Arnold, Regina
AU - Flippen-Anderson, Judith
AU - Karle, Isabella
PY - 1986
Y1 - 1986
N2 - 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.
AB - 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.
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U2 - 10.1021/jo00366a013
DO - 10.1021/jo00366a013
M3 - Article
AN - SCOPUS:0022442164
SN - 0022-3263
VL - 51
SP - 3148
EP - 3150
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -