Photochemical conversion of α-diazo-amides and -esters into β-lactams and β- and γ-lactones

Abstract

Summary N[(Alkoxycarbonyl)diazoacetyl]piperidines (3; R = Et and Bu^t) give both cis- and trans-fused β-lactams (4 and 5; R = Et and Bu^t) on photolysis, wheres N-[(alkoxycarbonyl)diazoacetyl]pyrrolidines (6; R = Et) and (6; R = Bu^t) give the β- and γ-lactones (7) and (8) respectively; photolysis of the N-[(t-butoxycarbonyl)- diazaoacetyl]-L-thiazolidine-4-carboxylic ester (9), however, gives both the β-lactams (10) and the γ-lactone (11).