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Diastereoselective reduction of cyclic bioactive Mannich ketones
The reduction of cyclic Mannich ketones having antibacterial activity showed poor stereoselectivity with L-Selectride ® , sodium trimethoxyborohydride and diisobutylaluminium hydride, while lithium aluminium hydride and, in particular, sodium borohydride often yielded a single stereoisomer. The size of the ring strongly influenced the stereocomposition of the reaction mixtures. An increased preference for the trans isomer was attributed to a weak intramolecular hydrogen bond between the OH anddoi:10.3998/ark.5550190.0005.704 fatcat:wfmdjalw3vclvchgixy6d4nahm