Asymmetric radical and anionic cyclizations of axially chiral carbamates.
Standard Boc, Alloc, and Cbz derivatives of N-2,4-dimethyl-6-iodophenyl-N-allyl anilines are axially chiral and can be readily resolved into atropisomers whose racemization barriers exceed 30 kcal/mol. The resolved axially chiral carbamates undergo radical and anionic cyclizations with high levels of chirality transfer from the N-Ar axis to the new stereocenter in the substituted dihydroindole products. The carbamate groups of the products are readily removed.
Guthrie
David B
DB
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Curran
Dennis P
DP
D000838:Anions / Q000737:chemistry; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000838:Anions; D002219:Carbamates; D005609:Free Radicals