Diphenylprolinol Silyl Ether as a Catalyst in an Enantioselective,Catalytic,Formal Aza [3+3] Cycloaddition Reaction for the Formation of Enantioenriched Piperidines

摘要

The piperidine ring system is one of the most common structural subunits in natural products and biologically significant compounds.The aza Diels-Alder reaction and the aza [3+3] cycloaddition reaction are straightforward synthetic methods for making piperidine ring systems.Several methods have been developed for formal aza [3+3] cycloaddition reactions,such as reactions of 1,3-cyclic sulfonates with C/N dianions,vinylogous amides with alpha,beta-unsaturated iminium ions,and aziridines with Pd-trimethylenemethane complexes.In spite of these formal aza [3+3] cycloaddition methods,and to the best of our knowledge,an enantioselective catalytic version has not been reported.