Development of catalytic direct addition reactions of unprotected aminoalkanes

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We tried to investigate the catalytic direct carbon-carbon bond forming reactions of aminoalkanes using a fluorenylidene moiety as a catalytic activator. In 1,4-addition reaction of a glycine ester to an alpha,beta-unsaturated carbonyl compound, we confirmed that catalytic turnover of the fluorenylidene moiety to form a carbon-carbon bond occurred. This result revealed that catalytic activation of N-unprotected aminoalkanes was possible by using the fluorenylidene group. We also found that a N-fluorenylimine could work as a nucleophile in the presence of a base catalyst and that it reacted with another type of imine to accomplish a catalytic imine-imine cross coupling reaction.