Catalytic asymmetric conjugate addition of isocyanoacetate to (Z)-3-substituted-2-(4-pyridyl)-acrylonitrile, a reactive class of Michael acceptor

Abstract

(Z)-3-Substituted-2-(4-pyridyl)-acrylonitriles, a reactive class of Michael acceptors obtained exclusively as a single (Z) isomer, reacted with un-substituted isocyanoacetate esters mediated by phase-transfer catalysis to give, after base promoted cyclisation, functionalized imines in up to 94% ee and as a single diastereoisomer.

Catalytic Enantioselective Isocyanide‐Based Reactions: Beyond Passerini and Ugi Multicomponent Reactions

“…The 3‐methly‐4‐nitroisoxazole substituent could be removed by treatment with KMnO 4 to deliver the pyrrolidines with a free carboxylic acid group. Recently, they further extended the protocol to include ( Z )‐3‐substituted‐2‐(4‐pyridyl)‐acrylonitriles in the reaction scope [50b] …”

Study of Ground State Interactions of Enantiopure Chiral Quaternary Ammonium Salts and Amides, Nitroalkanes, Nitroalkenes, Esters, Heterocycles, Ketones and Fluoroamides

“…The groups of Umani‐Ronchi, [21] Ricci and Bernardi, [22–26] Jørgensen, [27,28] Della Sala [29] and Albanese [30,31] provided notable synthetic applications of Cinchona derived ammonium species. Adamo and coworkers have reported some highly enantioselective reactions that make use of Cinchona ‐based quaternary ammonium salts [32–41] . Concomitantly, the groups of Waser and Vetticatt have reported the use of bifunctional quaternary ammonium salts in highly enantioselective α ‐fluorinations; [42] asymmetric cascade cyclizations; [43,44] Michael additions; [43] α‐ hydroxylations; [45] and α‐ chlorinations [46] …”

“…Adamo and coworkers have reported some highly enantioselective reactions that make use of Cinchona ‐based quaternary ammonium salts. [ 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ] Concomitantly, the groups of Waser and Vetticatt have reported the use of bifunctional quaternary ammonium salts in highly enantioselective α ‐fluorinations; [42] asymmetric cascade cyclizations;[ 43 , 44 ] Michael additions; [43] α‐ hydroxylations; [45] and α‐ chlorinations. [46] …”

Synthesis, optical and electrochemical properties, and photovoltaic performance of a panchromatic and near-infrared (D)2–π–A type BODIPY dye with pyridyl group or cyanoacrylic acid

“…BODIPY dye OMK-PY was prepared by reacting 4-pyridylacetonitrile hydrochloride with the compound 7 in the presence of NEt 3 . 27 BODIPY dye OMK-CA was prepared by typical Knoevenagel condensation of the compound 7 with cyanoacetic acid in the presence of piperidine.…”