Synthesis of chiral 3-substituted 3-amino-2-oxindoles through enantioselective catalytic nucleophilic additions to isatin imines

Abstract

This review collects the recent developments in the synthesis of chiral 3-substituted 3-amino-2-oxindoles based on enantioselective catalytic nucleophilic additions to isatin imines published since the beginning of 2015.

DABCO-Catalyzed Mono-/Diallylation of N-Unsubstituted Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates

“…Moreover, 3-substituted oxindoles are also heterocyclic frameworks and have widely existed in bioactive molecules [ 10 , 11 , 12 , 13 , 14 , 15 , 16 ]. Various methods of constructing 3-substituted oxindoles have been reported [ 17 , 18 , 19 ].…”

Synthesis and Biological Evaluation of Isatin Based Thiazole Derivatives

“…Isatin moiety is responsible for a wide spectrum of biological property such as anticancer and antiviral in many synthetically versatile molecules [8]. Isatin derived ketimines represent readily available synthetic precursors of the 3-amino-2-oxindole moiety via enantioselective Mannich type reactions [9,10]. Another indolebased moiety with proven anti-proliferative potential via inhibition treatment of gastrointestinal stromal tumors and advanced renal cell carcinoma [11].…”

Organocatalytic Direct Enantioselective Hydrophosphonylation of N-Unsubstituted Ketimines for the Synthesis of α-Aminophosphonates

“…Direct catalytic enantioselective addition to ketimines is an effective method for producing chiral amines with a tetrasubstituted carbon stereocenter under proton-transfer conditions. − The majority of the reactions use N -substituted ketimines, and the substituent on the nitrogen atom can tune reactivity and selectivity . However, these reactions require the protection and deprotection of the substituent to obtain N -unprotected amines, resulting in longer reaction steps and unwanted chemical waste formation.…”