%0 Journal Article %J Angewandte Chemie-International Edition %D 2019 %T Phosphite-Catalyzed C-H allylation of azaarenes via an enantioselective [2,3]-Aza-wittig rearrangement %A Motaleb, Abdul %A Rani, Soniya %A Das, Tamal %A Gonnade, Rajesh G. %A Maity, Pradip %X

A phosphite-mediated [2,3]-aza-Wittig rearrangement has been developed for the regio- and enantioselective allylic alkylation of six-membered heteroaromatic compounds (azaarenes). The nucleophilic phosphite adducts of N-allyl salts undergo a stereoselective base-mediated aza-Wittig rearrangement and dissociation of the chiral phosphite for overall C-H functionalization of azaarenes. This method provides efficient access to tertiary and quaternary chiral centers in isoquinoline, quinoline, and pyridine systems, tolerating a broad variety of substituents on both the allyl part and azaarenes. Catalysis with chiral phosphites is also demonstrated with synthetically useful yields and enantioselectivities.

%B Angewandte Chemie-International Edition %8 AUG %G eng %9 Article %3

Foreign

%4

12.257

%R 10.1002/anie.201906681