Preparation of (1R,1′R)-1,1′-(anthracene-9,10-diyl)bis(2,2,2-trifluoroethanamine): a chiral diamine with low basicity

Synthesis and Applications of tert-Butanesulfinamide

“…Recently, Virgili and co-workers applied the method developed by Prakash and co-workers to the TMAF mediated addition of TMSCF 3 to bis( N - tert -butanesulfinyl imine) 979 (eq ) . The desired adduct 980 was obtained as a single diastereomer in 88% yield and was then tested as a chiral solvating agent with the chiral carboxylic acid, ibuprofen.…”

Nucleophilic Trifluoromethylation of C=N Bonds

“…The sequence includes formation of N-sulfinimine, fluoride-promoted trifluoromethylation, which gave the product as a single diastereoisomer, and acidic removal of chiral auxiliary. [22] Reaction of a chiral N-isopropylsulfinamide was applied for the synthesis trifluoromethylated analogue of calcimimetic drug NPS R-568. [23] Scheme 13.…”

Highly Diastereoselective Synthesis of α‐Difluoromethyl Amines from N‐tert‐Butylsulfinyl Ketimines and Difluoromethyl Phenyl Sulfone

“…(1 R ,1′ R )‐1,1′‐(Anthracene‐9,10‐diyl)bis(2,2,2‐trifluoroethanamine), a chiral diamine with low basicity, was also successfully synthesized by Estivill et al. using the same strategy 4j. Not only did N ‐ tert ‐butylsulfinyl imines readily undergo electrophilic reactions with the Ruppert–Prakash reagent (Me 3 SiCF 3 ), but they also underwent the addition of fluorinated Reformatsky reagents to afford β‐branched α,α‐difluoro‐β‐amino esters 4i…”