Radical-mediated annulation reactions. A versatile strategy for the preparation of a series of carbocycles.
[reaction--see text] A series of novel 6-endo [4 + 2] and 7-endo [5 + 2] radical-mediated annulation reactions are described. These annulation sequences involve an intermolecular radical addition followed by intramolecular trapping with an allyltin moiety incorporated into the radical precursor fragment. This methodology allows for access to functionalized 6- and 7-membered carbocycles as well as bicyclic compounds with good to excellent levels of stereocontrol.
Sibi
M P
MP
Department of Chemistry, North Dakota State University, Fargo, North Dakota 58015, USA. mukund.sibi@ndsu.nodak.edu
Chen
J
J
Rheault
T R
TR
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D005609:Free Radicals; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis*; D009947:Organotin Compounds / Q000737:chemistry; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D005609:Free Radicals; D006844:Hydrocarbons, Cyclic; D009947:Organotin Compounds