Addition Reactions of Chloro- or Iodomethyllithium to Imines. Synthesis of Enantiopure Aziridines and beta-Chloroamines

作者:Concellon Jose M*; Rodriguez Solla Humberto; Bernad Pablo L; Simal Carmen
来源:Journal of Organic Chemistry, 2009, 74(6): 2452-2459.
DOI:10.1021/jo802596y

摘要

We report a novel, simple, and efficient synthesis of aziridines and 1-chloroalkan-2-amines by the reaction of imines derived from various aldehydes and p-toluenesulfonamide or benzenesulfonamide with iodoor chloromethyllithium, respectively. Both halogenated anions were generated in situ by treatment of diiodo- or chloroiodomethane with methyllithium at -78 or 0 degrees C. The reaction of in situ generated iodo- or chloromethyllithium could also be performed from chiral 2-aminoaldimines to yield enantiopure aziridines or (2S,3S)-2,3-diamino-1-chloroalkanes with high stereoselectivity.

  • 出版日期2009-3-20