1213137-26-8Relevant articles and documents
Catalytic Asymmetric Reduction of α-Trifluoromethylated Imines with Catecholborane by BINOL-Derived Boro-phosphates
He, Hualing,Tang, Xiaoxue,Cao, Yang,Antilla, Jon C.
, p. 4336 - 4345 (2021/03/01)
A catalytic enantioselective reduction of α-trifluoromethylated imines by a BINOL-derived boro-phosphate employing catecholborane as hydride source has been developed. This method provides an efficient route to prepare synthetically useful chiral α-triflu
Enantiodivergent approach to trifluoromethylated amines: A concise route to both enantiomeric analogues of calcimimetic NPS R-568
Fernandez, Inmaculada,Valdivia, Victoria,Alcudia, Ana,Chelouan, Ahmed,Khiar, Noureddine
experimental part, p. 1502 - 1509 (2010/06/15)
Reported herein is a straightforward and enantiodivergent synthesis of both enantiomers of trifluoromethylated analogues of calcimimetic NPS R-569 in a highly estereoselective manner. The synthesis features a diastereoselective synthesis of the N-(isopropylsulfinyl)imine unit by the "DAG methodology" and a diastereoselective addition of Ruppert Prakash's reagent to the imine as the key steps. No protecting groups were necessary, permitting an atom economic synthesis in only six steps. Further addition reactions of the CF3 anion to different N-(isopropylsulfinyl)imines were performed to demonstrate the suitability of the sulfinyl substituent to balance perfectly reactivity and diastereoselectivity.