1214919-08-0

Basic information

• Product Name: (R)-2-(3-hydroxy-1-methyl-2-oxoindolin-3-yl)ethyl 4-methylbenzenesulfonate
• Synonyms: (R)-2-(3-hydroxy-1-methyl-2-oxoindolin-3-yl)ethyl 4-methylbenzenesulfonate
• CAS NO: 1214919-08-0
• Molecular Weight: 361.419
• Mol File: 1214919-08-0.mol

Chemical Properties

• CAS DataBase Reference: (R)-2-(3-hydroxy-1-methyl-2-oxoindolin-3-yl)ethyl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(3-hydroxy-1-methyl-2-oxoindolin-3-yl)ethyl 4-methylbenzenesulfonate(1214919-08-0)
• EPA Substance Registry System: (R)-2-(3-hydroxy-1-methyl-2-oxoindolin-3-yl)ethyl 4-methylbenzenesulfonate(1214919-08-0)

Safety Data

• Hazardous Substances Data: 1214919-08-0(Hazardous Substances Data)

Upstream product

• 1178982-16-5 (R)-3-allyl-3-hydroxy-1-methylindolin-2-one 
• 98-59-9 p-toluenesulfonyl chloride 
• 2058-74-4 1-methyl-1H-indole-2,3-dione 

Relevant articles and documents

Direct asymmetric vinylogous aldol reaction of allyl ketones with isatins: Divergent synthesis of 3-hydroxy-2-oxindole derivatives

6 in 1: The highly enantioselective title reaction is mediated by a bifunctional catalyst and leads to E-configured vinylogous aldol products (see scheme). These products are used as common intermediates in the synthesis of six biologically active 3-hydroxy-2-oxindole derivatives (e.g., CPC-1). Computational studies indicated that the observed stereoselectivity is a result of favorable secondary π-π* and H-bonding interactions in the transition state. Copyright

BINOL derivatives-catalysed enantioselective allylboration of isatins: Application to the synthesis of (: R)-chimonamidine

The asymmetric synthesis of the 3-allyl-3-hydroxyoxindole skeleton was accomplished in yields up to 99% via a metal-free and enantioselective allylation of isatins (90-96% ee) using BINOL derivatives as catalysts and an optimized allylboronate. This methodology was applied at a gram-scale to the synthesis of the natural product (R)-chimonamidine. This journal is

A Diamino Alcohol Catalyzed Enantioselective Crossed Aldol Reaction of Acetaldehyde with Isatins – A Concise Total Synthesis of Antitumor Agents

Enantioselective crossed aldol reactions of isatin derivatives and acetaldehyde have been developed with a series of simple diamino alcohol catalysts to afford 3-substituted 3-hydroxyindolin-2-ones in high chemical yields (up to 95 %) and optical purities (up to 92 % ee). The synthetic potential of the present protocol has been demonstrated by concise, enantioselective, protecting-group-free, and transition metal-free total syntheses of antitumor and antiviral agents with the tryptanthrin architecture, that is, phaitanthrin B and cephalanthrin A, along with the biologically active indolidine alkaloids chimonamidine and donaxaridine as well as the formal synthesis of CPC-1. The highly enantioselective outcome of this catalytic crossed aldol reaction was evaluated by calculating the Gibbs free energies of the possible transition states.