Synthesis of Optically Active Deuterated Primary Amines via Reduction of N-tert-Butanesulfinyl Aldimines

Abstract

Optically active deuterated primary amines have been obtained with 78-98% ee's from chiral N-tert-butanesulfinyl aldimines via reduction with N-Selectride and subsequent alcoholysis.

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

“…In 2014 Shi et al prepared and reduced deuterated sulfinylaldimines to access chiral deuterated primary amines. [31] They obtained the expected compounds with good yields and good diastereoselctivities (Scheme 23). In the same year, Suna et al developed a diastereoselective hydroxymethylation of cyclic ketimines.…”

Chiral N‐tert‐Butylsulfinyl Imines: New Discoveries

“…Optically active deuterated primary amines 7 were easily prepared starting from deuterated N ‐ tert ‐butylsulfinyl aldimines 5 , by reduction with N ‐selectride, to give 6 , followed by desulfinylation with HCl in EtOH (Scheme 3). [13] …”

Progress in asymmetric biomimetic transamination of carbonyl compounds

“…In 2011, Shi and coworkers reported an effective chiral basecatalyzed transamination of a-keto esters. 34 Various chiral bases were examined with ethyl 2-oxo-4-phenylbutanoate (36) as the substrate and o-ClPhCH 2 NH 2 (37) as the nitrogen source (Scheme 13). Up to 69% ee was obtained with quinine derived This journal is © The Royal Society of Chemistry 2015 catalyst 45.…”