In memory of Professor Rolf Huisgen
Abstract
Catalytic asymmetric 1,3-dipolar cycloaddition reactions of activated isocyanides
with various 2π dipolarophiles have been intensively studied, affording a wide range
of enantioenriched five-membered N-heterocycles. In sharp contrast, the catalytic
enantioselective higher-order cycloaddition of activated isocyanides has not been
achieved yet. We present here our recent work on the development of an unprecedented
silver-catalyzed highly diastereo- and enantioselective [3+3] cycloaddition of activated
isocyanides with azomethine imines. This method features high efficiency, good to
excellent stereocontrol, wide substrate scope, as well as operational simplicity.
It is also noteworthy that the same catalytic system was proved to be suitable for
not only the late-stage functionalization of complex bioactive molecules but also
the kinetic resolution of racemic azomethine imines.
1 Introduction
2 Results and Discussion
3 Summary and Outlook
Key words
heterocycles - cycloaddition - kinetic resolution - diastereoselectivity - enantioselectivity
