Stereochemical differentiation in the reactions of organometallic reagentswith levoglucosenone and some of its dihydro derivatives

Authors
Tsypysheva, IP Valeev, FA Vasil'eva, EV Spirikhin, LV Tolstikov, GA
Citation
Ip. Tsypysheva et al., Stereochemical differentiation in the reactions of organometallic reagentswith levoglucosenone and some of its dihydro derivatives, RUSS CHEM B, 49(7), 2000, pp. 1237-1240
Citations number
17
Categorie Soggetti
Chemistry
Journal title
RUSSIAN CHEMICAL BULLETIN
ISSN journal
10665285 → ACNP
Volume
49
Issue
7
Year of publication
2000
Pages
1237 - 1240
Database
ISI
SICI code
1066-5285(200007)49:7<1237:SDITRO>2.0.ZU;2-F
Abstract
The reactions of methylmanganese iodide with levoglucosenone, its dihydro d erivative, and 1,6-anhydro-3-deoxy-4- O-methyl-beta-D-erythro-hexopyran-2-u lose were found to be highly diastereoselective compared to the reactions o f Li-, Mg-, and Cu-based reagents. This specific feature of the manganese r eagent is due to the enhanced tendency of manganese for chelation.