Et3B-induced radical addition of N,N-dichlorosulfonamide to alkenes and pyrrolidine formation via radical annulation.
A highly regioselective radical addition of N,N-dichlorobenzenesulfonamide (dichloramine-B) to 1-alkenes is achieved at -78 degrees C by the use of triethylborane as a radical initiator. The reaction of 1,3-dienes with N,N-dichlorosulfonamide in the presence of Et(3)B regioselectively provides N-chloro-N-allylamide derivatives. N-chloro-N-allylamides thus obtained react with a variety of alkenes to furnish pyrrolidine derivatives in good yields. A radical annulation reaction among N,N-dichlorosulfonamide, 1,3-dienes, and alkenes has been developed.
Tsuritani
Takayuki
T
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan.
Shinokubo
Hiroshi
H
Oshima
Koichiro
K