3??Chlorooxindoles: Versatile Starting Materials for Asymmetric Organocatalytic Synthesis of Spirooxindoles

…, M Oeeren, I Jaerving, MRJ Elsegood…

Index: Noole, Artur; Oseka, Maksim; Pehk, Tonis; Oeeren, Mario; Jaerving, Ivar; Elsegood, Mark R. J.; Malkov, Andrei V.; Lopp, Margus; Kanger, Tonis Advanced Synthesis and Catalysis, 2013 , vol. 355, # 5 p. 829 - 835

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Citation Number: 33

Abstract

The dual nucleophilic/electrophilic character of C-3 in 3-chlorooxindoles 7 provides an excellent opportunity for constructing an all-carbon quaternary center at this position by organocatalytic cascade reactions. Thus, increased acidity of the C H bond due to the presence of chlorine renders the 3-position more nucleophilic, while the chloride serves as a good leaving group for the subsequent cyclization step. ... Herein, we present a new reaction of 3-chlorooxindoles 7 with α,β- ...