Tandem N-Alkylation—C-Allylation Reaction of α-Imino Esters with Organoaluminums and Allyltributyltin.
✍ Scribed by Yasuki Niwa; Makoto Shimizu
- Publisher
- John Wiley and Sons
- Year
- 2003
- Weight
- 122 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0931-7597
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Synthesis of N-Alkoxycarbonyl-3-substituted Tetramic Acids and Functionalized Enols via C-Acylation Reactions of Active Methylene Compounds with N-Hydroxysuccinimide Esters of N-Alkoxycarbonylα-amino Acids. -A new, mild, and advantageous approach is used for the preparation of the title compounds,
Reaction of 2,3,4,6-tetra-O-acetyl-1,5-anhydro-o-arubino-hex-l-enitol (1; 2hydroxyglucal tetraacetate) with 1.0-1.5 mol of primary, secondary, or tertiary alcohols, in the presence of 0.1-1.0 mol of N-iodosuccinimide (NIS) in acetonitrjle as solvent, afforded the a anomers of alkyl 3-deoxyhex-2-eno