Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5217068 | Tetrahedron | 2014 | 7 Pages |
Abstract
Highly diastereoselective 1,2-dichlorination of glycals has been achieved at room temperature conditions in good to excellent yields using a milder, more convenient, less hazardous reagent combination NCS/PPh3 giving only one major product out of four possible diastereomers [either α-gluco (2) or α-manno (4)] depending upon the substituents. The diastereoselectivity is maximum (100% α/β-selectivity as well as cis/trans selectivity) for d-galactal and l-rhamnal derivatives. Detailed studies showed that solvent and substituent effects play a significant role in determining the product distribution.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Altaf Hussain, Debaraj Mukherjee,