Tetrahedron

A new role for L-ascorbic acid: Michael donor to α, β-unsaturated carbonyl compounds

…, R Arnold, T Mohacsi, I Karle, J Flippen-Anderson

文献索引：Fodor, Gabor; Arnold, Regina; Mohacsi, Tivadar; Karle, Isabella; Flippen-Anderson, Judith Tetrahedron, 1983 , vol. 39, # 13 p. 2137 - 2145

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被引用次数: 59

摘要

In a novel Michael-type reaction L-ascorbic acid (1) undergoes addition to acrolein to give the tricyclic hemiacetal lactone 3. The constitution and relative configuration of 3 was studied by a combination of NMR and IR spectroscopy. Ultimately, the structure of 3 was determined by X-ray crystallography. The absolute stereochemistry follows from the known chirality of C- 4 and C-5 of L-ascorbic acid. A mechanism for the reaction, including its steric course, is ...