Journal of the American Chemical Society, Vol.135, No.51, 19103-19106, 2013
1,5-Rhodium Shift in Rearrangement of N-Arenesulfonylazetidin-3-ols into Benzosultams
Benzosultams are synthesized in an enantiopure form starting from alpha-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by beta-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.