DOI: 10.1021/acs.joc.5c02916 ISSN: 0022-3263
Base-Mediated Cyclization of N -Benzyl Ketimines with Diynes: Conditions-Controlled Switching between N -Vinyl Pyrroles and 2 H
Ivan A. Bidusenko, Elena Yu Schmidt, Igor A. Ushakov, Alexander V. Vashchenko, Boris A. TrofimovAbstract
Semistabilized azaallyl anions, generated from N-benzyl ketimines in the NaOtBu/DMSO superbase medium, undergo conditions-controlled formal [3 + 2] or [4 + 3] cyclization with diaryldiynes. Consequently, selective switchable syntheses of triarylsubstituted α-arylated N-vinyl pyrroles (in up to 64% yield) and tetraarylated 2H-azepines (in up to 75% yield) have been developed. The synthetic value of this strategy has been validated by successful gram-scale syntheses of both products.