850924-08-2Relevant academic research and scientific papers
The isopropylsulfinyl group: A useful chiral controller for the asymmetric aziridination of sulfinylimines and the organocatalytic allylation of hydrazones
Fernandez, Inmaculada,Valdivia, Victoria,Gori, Beatrice,Alcudia, Felipe,Alvarez, Eleuterio,Khiar, Noureddine
, p. 1307 - 1310 (2005)
(Chemical Equation Presented) A comparative study shows that the isopropylsulfinyl group for which an enantiodivergent and highly diastereoselective approach is reported behaves better than the tert-butylsulfinyl and p-tolylsulfinyl groups, both in terms
Multicomponent synthesis of chiral sulfinimines
Roe, Caroline,Hobbs, Heather,Stockman, Robert A.
supporting information; experimental part, p. 2704 - 2708 (2011/04/15)
Two oxathiozolidine-S-oxide templates have been developed and used in a four-component coupling protocol for the synthesis of a wide range of chiral sulfinimines in high enantiomeric excesses. The templates can be synthesized from cheap commodity chemicals in three steps in high yields. Furthermore the template is easily recovered in high yields for recycling.
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.
