Efficient asymmetric synthesis of trifluoromethylated β-aminophosphonates and their incorporation into dipeptides.

نویسندگان

  • Kostiantyn V Turcheniuk
  • Kateryna O Poliashko
  • Valery P Kukhar
  • Alexander B Rozhenko
  • Vadim A Soloshonok
  • Alexander E Sorochinsky
چکیده

Addition of anions derived from dialkyl methylphosphonates to (Ss)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine afforded (Ss,R) addition adducts in moderate to good yield (53-75%) with excellent diastereoselectivity (94-95% de). After selective removal of the N-sulfinyl group, dipeptides containing enantiomerically pure diethyl 2-amino-3,3,3-trifluoropropylphosphonate were synthesized to investigate the influence of the trifluoromethyl substituent on N-terminal coupling.

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عنوان ژورنال:
  • Chemical communications

دوره 48 94  شماره 

صفحات  -

تاریخ انتشار 2012