Related Experiment Video
Updated: Apr 2, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Access to Chiral Oxindoles via Ir-Catalyzed Asymmetric Pudovik Addition/[1,2]-Phospha-Brook Rearrangement/Allylation
Bo-Bin Chen1, Zhi-Yuan Yi1, Xiu-Qin Dong1
1Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, People's Republic of China.
Abstract:
An asymmetric catalytic Pudovik addition/[1,2]-phospha-Brook rearrangement/allylation reaction of readily available isatins, phosphites, and vinyl ethylene carbonate enabled by a chiral iridium catalyst was developed in a one-pot fashion. A wide range of enantioenriched oxindole derivatives containing two adjacent stereocenters could be obtained in good to high yields with excellent diastereoselectivity and enantioselectivity (65-99% yield, 7:1 to >20:1 dr, and generally 99% ee). This cascade protocol owned the advantages of readily available starting materials, high regio-/diastereo-/enantioselectivity, and good substrate scope generality.
Related Concept Videos
Regioselectivity of Electrophilic Additions-Peroxide Effect
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Radical Anti-Markovnikov Addition to Alkenes: Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
