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Stereoselective Synthesis of an Aminocyclopentitol Analog of α-l-Fucose via an Allylic Bromohydrin
31 December 2000 (online)
Selective opening of allylic epoxide 4 with lithium bromide in acetic acid provides an allylic bromohydrin (5). Chemo- and stereoselective hydrogenation of the corresponding benzyl carbamate 6 and intramolecular cyclization gives, after deprotection, (1R,2R,3R,4R,5R) 4-amino-5-methyl-cyclopentane-1,2,3-triol 3, an analog of α-l-fucose. This synthetic sequence provides one of the few stereoselective approaches to alpha-configurated aminocyclopentitols.
aminations - amino alcohols - carbohydrates - glycosidases - stereoselective synthesis