REDUCTIVE PINACOL REARRANGEMENT REACTION

摘要

PURPOSE:To obtain an optically pure 2-aryl- or 2-alkenyl-1-propanol, by reacting alpha-mesyloxyketone with respective specific two kinds of organoaluminum compounds in combination to carry out reductive pinacol rearrangement reaction. CONSTITUTION:alpha-Mesyloxyketone is reactd with a compound expressed by the formula R2'AlH (R' is 2-10C aliphatic hydrocarbon group, preferably ethyl or isobutyl) and a compound expressed by the formula R3''Al or formula R2AlX (R'' is 1-15C aliphatic hydrocarbon group, preferably methyl, ethyl, propyl, butyl or isobutyl; X is halogen, preferably Cl) in combination to carry out the reductive reaction of the carbonyl group and pinacol rearrangement reaction to afford the aimed 2-aryl- or 2-alkenyl-1-propanol useful for synthesizing natural products or medicines, particularly ibuprofen (antipyretic and analgesic eliminator) in high optical purity.