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A ruthenium complex was found to catalyze the hydrogenation of chiral esters without the loss of their optical purities under mild and neutral conditions. This method can avoid a violent quench step and an extraction step which accompany conventional reduction using metal hydride reagents such as sodium borohydride and lithium aluminum hydride.
ROH-induced decomposition of the strained 7,7-diphenyl-6-oxabicyclo[3.2.0]hept-1-ene 1 was investigated in detail. The selective formation of the endo double-bonded alkene 3 was observed for the reaction with H 2 O or MeOH. Alternatively, the reaction with hexafluoro-2-propanol or acetic acid exclusively afforded the exo double-bonded alkene 5. The dramatic ROH effect on the product distribution...
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