ChemInform Abstract: Nonracemic α-Fluoro Aldehydes: Asymmetric Synthesis of 4-Deoxy-4-fluoro-D-arabinopyranose.

✍ Scribed by F. A. DAVIS; P. V. N. KASU; G. SUNDARABABU; H. QI

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 40 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199812066

✦ Synopsis

Nonracemic α-Fluoro Aldehydes: Asymmetric Synthesis of 4-Deoxy-4-fluoro-D-arabinopyranose.

-The first enantioselective synthesis of epimerizable α-fluoro aldehyde (V) and its utility as chiral building block by the asymmetric synthesis of the title pyranose (XI) is described. The precursor for aldehyde (V), the enantiopure fluorohydrin (IV), is readily available via reduction of carboximide (III). The transformation of aldehyde (V) to the target noncarbohydrate proceeds without epimerization of the α-fluoro stereogenic center. -(DAVIS, F.