Regio- and stereocontrol elements in Rh(II)-catalyzed intramolecular C-H insertion of α-diazo-α-(phenylsulfonyl)-acetamides

(matrix presnted) Intramolecular C-H insertion reaction of α-diazo-α-(phenylsulfonyl)acetamides proceeded with high regio- and stereoselectivities to afford highly functionalized y-lactams predominantly or exclusively. The high regioselectivity was attributed to the use of the phenylsulfonyl moiety, which altered electron density at the carbenoid center and exerted a steric effect during the insertion reaction. Also described herein are three control elements to determine regioselectivity, which are amide conformational, stereoelectronic, and substituent effects.