We report herein an unprecedented
atroposelective dynamic kinetic
resolution of Bringmann’s lactones with C-nucleophiles. By
the use of activated isocyanides as the reagent, a wide range of novel
axially chiral oxazole-substituted biaryl phenols were accessed in
high yields with high enantioselectivities. Key to the success of
this process lies in the tandem atroposelective addition of isocyanides
to the lactone substrate followed by a rapid cyclization, overcoming
the challenge of stereochemical leakage induced by lactol formation.
Herein, we report an unprecedented strategy for the simultaneous construction of a remote C−N stereogenic axis and three contiguous stereogenic carbon centers via silver-catalyzed desymmetrizative [3 + 2] cycloaddition of prochiral N-aryl maleimides with activated isocyanides. This method features operational simplicity, wide substrate scope, high efficiency, and good to excellent stereoselectivity. Notably, it represents the first example of catalytic enantioselective synthesis of C−N atropisomers with the use of activated isocyanides.
The catalytic reaction of biaryl lactams with activated isocyanides is reported for the first time. By employing a cooperative catalytic system, oxazole-containing axially chiral biaryl anilines were obtained in high...
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