Stereoselective addition reactions of chiral N-benzylidene-p-toluenesulfinamides. Asymmetric syntheses of .beta.- and .gamma.-amino acids

Diastereoselective Addition of Organomagnesium and Organolithium Reagents to Chiral Trifluoromethyl N‐tert‐Butanesulfinyl Hemiaminals

“…The same facial diastereoselectivity, though greater for the allylation reaction relative to the alkylation with Grignard reagents, can be explained by a chelated transition‐state model TS‐2 (Scheme ) 15a,16,21. In this cyclic transition state where both the sulfinyl oxygen and the imine nitrogen are coordinated to the magnesium, the approach of the allyl Grignard reagent occurs also from the re face.…”

Application of Chiral Sulfinamides into Formation and Reduction of Sulfinylketimines to Obtain Valuable α‐Chiral Primary Amines

“…Storace et al investigated different synthetic pathways to obtain DMP 777, a human leukocyte elastase inhibitor. [47] In one of these synthetic routes, they prepared a sulfinylketimine using Hua's method [5] and then reduced this sulfinylketimine to obtain a key intermediate in the synthesis of DMP 777 as shown in Scheme 40. [48] Both diastereoisomers could be separated by careful column chromatography.…”

1,1,1-Trifluoropropan-2-ammonium triflate enantiomers: stereoselective synthesis and direct use in reaction with epoxides

“…Alternatively, a transition state involving a sulfinimine in the s-trans conformation could be considered as well (not shown). 22,23 In contrast, Nsulfinylimine reduction with NaBH 4 is proposed to proceed via a chelated transition state. 17 With the Z-imine 5a, this would give TS-3, featuring Re-face attack, which was not observed.…”