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Uma serie de aldeidos, alquinois e benzilaminas foram submetidos a reacao, por catalise mediada por CuCl, na formacao de hidroxi-benzilaminas funcionalizadas. O procedimento permite a utilizacao de aldeidos alquilicos e arilicos. Substratos representativos foram convertidos em alcaloides ciclicos de cinco e seis membros atraves da reacao concomitante de N-debenzilacao e reducao total da ligacao tripla promovida por Pd, seguido de ciclizacao tipo Mitsunobu. A number of aldehydes, alkynols and benzylamines were submitted to A 3 -coupling reaction, under CuCl catalysis, giving strategically functionalized hydroxy-propargylamines. The procedure allows the use of alkyl as well as aryl aldehydes. Representative substrates were converted into fiveand six-membered cyclic alkaloids by sequential one-pot N-debenzylation/triple bond reduction promoted by Pd, followed by a Mitsunobu-type cyclization.

A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids

A³-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids