Synthesis of (2S,3S)-β-(trifluoromethyl)-α,β-diamino acid by Mannich addition of glycine Schiff base Ni(II) complexes to N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine

N‐tert‐Butylsulfinyl‐3,3,3‐trifluoroacetaldimine: Versatile Reagent for Asymmetric Synthesis of Trifluoromethyl‐Containing Amines and Amino Acids of Pharmaceutical Importance

“…Nevertheless, the authors also reported the reaction between 92 (an achiral Ni II complex of glycine Schiff base) and imine ( S s )‐ 7 . The addition readily proceeded in the presence of 15 mol‐% of DBU and gave rise to major diastereomer 93 (Scheme ) with good isolated yield.…”

Trifluoromethyl aldimines: an overview in the last ten years

“…Therefore, to overcome these drawbacks, the Authors have considered appropriate to use alternative nucleophilic glycine equivalent that can be recovered and recycled after formation of the target product. Thus, the same research group in a subsequent work 48 have employed Ni(II) complexes derived from glycine Schiff bases with the hope to obtain α,β-diamino acids on a relatively large scale.…”

Development and Evaluation of Different Methods for Preparation of Fluorine‐Containing (R)‐ and (S)‐N‐tert‐Butanesulfinyl–aldimines

“…N ‐ tert ‐butanesulfinyl‐imines 2 , inspired by the seminal work of Ellman group, [37, 38] possess quite remarkable stereocontrolling properties, high reactivity and can be used for selective and highly efficient installation of 2,2,2‐trifluoro‐1‐(amino)ethyl moiety. As demonstrated by numerous research groups, most notably by O′Shea, Qing, Shibata, [44, 45] Roeschenthaler and Han, CF 3 ‐imines 2 easily react with virtually any type of nucleophiles, including Baylis‐Hillman and Friedel‐Crafts reactions, affording the target 2,2,2‐trifluoro‐1‐(amino)ethyl containing compounds with excellent yields and diastereoselectivity. Considering the wealth of literature data one can assert that chemistry of CF 3 ‐imines 2 is a mature field of a proven, exceptionally high synthetic value.…”