A (2R, 4S)-trans-disubstituted pyrrolidine ring system was constructed by employing iodine- mediated oxidative cyclization of (1R)-N-[1-(4-bromophenyl)-3-butenyl] acetamide 3 as a key step. The resulting diastereomeric mixture of (2R)-2-aryl-4-acetoxypyrrolidine 4 was stereoselectively converted to the side-chain of a novel ultra-broad-spectrum carbapenem 1, via (2R, 4R)-2-aryl-4-hydroxypyrrolidine 7.
[Zhan, Weiqiang; Jiang, Yi; Brodie, Peggy J.; Kingston, David G. I.; Liotta, Dennis C.; Snyder, James P. Organic Letters, 2008 , vol. 10, # 8 p. 1565 - 1568]
