Recent developments in the catalytic asymmetric synthesis of indolin-3-one derivatives
Atul J Dolas1, Arun Patel1, Imtiyaz A Shah1
1Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India. indresh.chemistry@gmail.com.
Abstract:
2,2-Disubstituted indolin-3-ones, which are essential components in many manufactured chemicals, dyes, and naturally occurring bioactive alkaloids, have emerged as exciting synthetic targets. Much attention has been paid to accessing these units, particularly in an asymmetric fashion, during the last decade. In this review article, we discuss the current state of available methods with existing mechanistic pathways for accessing chiral indolin-3-one derivatives under various catalytic systems. This overall presentation of asymmetric catalytic protocols to access 2,2-disubstituted or fused indolin-3-ones with an aza-quaternary centre is categorized based on the reaction modes of 2-substituted-3H-indole-3-one derivatives or other similar protocols.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
