Catalytic atroposelective dynamic kinetic resolution of biaryl lactones with activated isocyanides

L Qian, LF Tao, WT Wang, E Jameel, ZH Luo… - Organic …, 2021 - ACS Publications
L Qian, LF Tao, WT Wang, E Jameel, ZH Luo, T Zhang, Y Zhao, JY Liao
Organic Letters, 2021ACS Publications
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 …
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.
ACS Publications
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