522629-15-8Relevant articles and documents
Continuous-flow stereoselective reduction of prochiral ketones in a whole cell bioreactor with natural deep eutectic solvents
Annunziata, Francesca,Conti, Paola,Gandolfi, Raffaella,Guaglio, Alessandra,Tamborini, Lucia
, p. 950 - 956 (2022/02/02)
Immobilized whole cells of Rhodotorula rubra MIM147 were used in a packed bed flow reactor for the enantioselective reduction of β-ketonitriles and for the efficient production of a key building block for the synthesis of the antidepressant drug duloxetin
Direct Catalytic Asymmetric Addition of Alkylnitriles to Aldehydes with Designed Nickel–Carbene Complexes
Saito, Akira,Adachi, Shinya,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information, p. 8739 - 8743 (2021/03/16)
A direct catalytic asymmetric addition of acetonitrile to aldehydes that realizes over 90 % ee is the ultimate challenge in alkylnitrile addition chemistry. Herein, we report achieving high enantioselectivity by the strategic use of a sterically demanding NiII pincer carbene complex, which afforded highly enantioenriched β-hydroxynitriles. This highly atom-economical process paves the way for exploiting inexpensive acetonitrile as a promising C2 building block in a practical synthetic toolbox for asymmetric catalysis.
Synthesis of β-hydroxyamides through ruthenium-catalyzed hydration/transfer hydrogenation of β-ketonitriles in water: Scope and limitations
González-Fernández, Rebeca,Crochet, Pascale,Cadierno, Victorio
, p. 90 - 101 (2019/06/18)
A cascade process for the straightforward one-pot conversion of β-ketonitriles into β-hydroxyamides is presented. The process, that proceeds in water employing the arene-ruthenium(II) complex [RuCl2(η6-p-cymene){P(4-C6H4F)2Cl}] as catalyst in combination with sodium formate, involves the initial hydration of the β-ketonitrile substrates to generate the corresponding β-ketoamide intermediates, which subsequently undergo the transfer hydrogenation (TH) of the carbonyl group. Employing a family of forty different β-ketonitriles, featuring diverse substitution patterns, the scope and limitations of the process have been established.
