Rhodium-catalyzed diastereoselective 1,2-addition of arylboronic acids to chiral trifluoroethyl imine

Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas

“… In this context, one of quite successful findings is ( S )- or ( R )- N - tert -butylsulfinyl-3,3,3-trifluoroacetaldimine 27 (Scheme ). − In molecule 27 the trifluoromethyl − and tert -butylsulfinyl − groups are two strongly stereocontrolling substituents usually providing excellent stereochemical outcome of nucleophilic additions across the CN double bond. Compound 27 is readily available in both ( S ) and ( R ) enantiomeric forms, and can be prepared on a large scale .…”

Highly Stereoselective aza‐Baylis–Hillman Reactions of CF3‐Sulfinylimines: Straightforward Access to α‐Methylene β‐CF3 β‐Amino Acids

“…This reaction has been extensively studied in racemic and asymmetric versions and can be extended to various Michael acceptors (mainly acrylates, but also vinyl ketones, cyclic enones, and acroleins) and several activated aldimines (sulfonylimines, sulfinylimines, phosphinylimines) by using different kinds of catalysts (phosphines or tertiary amines). [40,41] Recently, N-tert-butylsulfinylimines [42][43][44] and, in particular, their fluorinated counterparts [45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62] have received much attention as a result of their potential to undergo various nucleophilic additions in high yields with high diastereoselectivity. Although the corresponding adducts were obtained with good diastereoselectivities [up to 88 % diastereomeric excess (de)], the chemical yields were rather moderate.…”

Chiral Sulfur Compounds Studied by Raman Optical Activity: tert‐Butanesulfinamide and its Precursor tert‐Butyl tert‐Butanethiosulfinate

“…[1][2][3][4][5] One of the simplest sulfinamide, tert-butanesulfinamide, has been established as a versatile reagent for the asymmetric synthesis of aminecontaining compounds, which are prominent in drugs, agrochemicals, and naturally occurring materials. 3 Specifically, tert-butanesulfinamides have been applied in the synthesis of enantiopure sulfinylimines, 6-10 a-branched amines, 6,7,9,[11][12][13] allylic amines, [14][15][16] propargylic amines, 17,18 a-amino acid and b-amino acid derivatives, 8,19-21 1, 2-amino alcohols, 17,22,23 1, 3-amino alcohols, 24,25 1, 2-diamine, 26,27 1, 3-diamines, 28,29 fluorinated amine derivatives, [30][31][32][33][34] a-organometallic amines, 35,36 aziridine, 23,37 and cyclic sulfinamides. 38,39 In asymmetric catalysis, tert-butanesulfinamides are increasingly being incorporated within chiral ligand and organocatalyst frameworks.…”