02105nas a2200157 4500008004100000245010900041210006900150260000800219520149800227100001901725700001701744700001501761700002401776700001801800856012901818 2019 eng d00a Phosphite-Catalyzed C-H allylation of azaarenes via an enantioselective [2,3]-Aza-wittig rearrangement 0 aPhosphiteCatalyzed CH allylation of azaarenes via an enantiosele cAUG3 a

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.

1 aMotaleb, Abdul1 aRani, Soniya1 aDas, Tamal1 aGonnade, Rajesh, G.1 aMaity, Pradip uhttps://library.ncl.res.in/content/phosphite-catalyzed-c-h-allylation-azaarenes-enantioselective-23-aza-wittig-rearrangement