Lewis acid-catalyzed aldol condensation of 2-trimethylsilyloxy-4-trifluoromethylfuran (2a) with aldehydes was found to proceed in a regio- and diastereoselective manner to give the 5-substituted 4-trifluoromethyl-2 (5H)-furanone (4) in good yield. The aldol product (4a) derived from benzyloxyacetaldehyde was successfully converted to the branched sugar (12), the first reported example of a trifluoromethylated branched sugar, and its crystal structure was determined by X-ray analysis.
|Journal||Chemical and Pharmaceutical Bulletin|
|Publication status||Published - 1985|
SAWADA, KOSUKE., Kitagawa, O., TAGUCHI, TAKEO., HANZAWA, YUJI., KOBAYASHI, YOSHIRO., & IITAKA, YOICHI. (1985). Studies on Organic Fluorine Compounds. XLVII. Synthesis of Trifluoromethylated Sugars through the Aldol Reaction of 2-Trimethylsilyloxy-4-trifluoromethylfuran. Chemical and Pharmaceutical Bulletin, 33(10), 4216-4222.