| Summary: | 碩士 === 國立臺灣師範大學 === 化學系 === 104 === A method to build the framework of bicyclo[2.2.2]octanes via 2-amino-1,3-dienes system with quinine-derived primary amine catalyst was disclosed. According to optimized conditions, cyclohexenones and 2-aryllidene-1,3-indanediones were dissolved in toluene at the room temperature, then 20 mol% of primary amine catalyst and 20 mol% of benzoic acid were added. The substituted bicyclo[2.2.2]octanones, bearing one spiro quaternary carbon and three chiral centers, were obtained in high yields (up to 91 %), excellent diastereoselective ( up to >20:1 dr) and enantioselective (98% ee). This reaction was also operated with cinnamaldehyde, 1,3-indandione and cyclohexenone, through Knoevenagel condensation/ [4+2] cycloaddition in one-pot manner to get desired product bicyclic with the high level of stereoselectivities (>20:1 dr, 97% ee).
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