Preparation and in situ use of unstable -alkyl α-diazo-γ-butyrolactams in Rh-catalyzed X-H insertion reactions.

-Alkyl α-diazo-γ-butyrolactams, previously found to be unstable and to undergo unproductive dimerization to bishydrazones, were successfully converted immediately to various X-H insertion products with alcohols, aromatic amines and thiols via an in situ Rh-catalyzed reaction. With aliphatic amines or unreactive, sterically hindered anilines, the reactions tended to yield enamine adducts.