Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles

• Published in: Chirality
• Main Authors: Kumar, Naveen, Kumar, Akshay, Sahoo, Subash Chandra, Chimni, Swapandeep Singh
• Other Authors: Council of Scientific and Industrial Research, India
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2020
• Subjects: Spiro; Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/chir.23284; https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.23284; https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chir.23284

Abstract Candida antarctica (CAL‐B) lipase‐catalyzed resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles has been performed to obtain ( R )‐1,3‐dialkyl‐3‐acetoxymethyl oxindoles with up to 99% ee and ( S )‐1,3‐dialkyl‐3‐hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming ( S )‐3‐allyl‐3‐hydroxymethyl oxindole to (3 S )‐1′‐benzyl‐5‐(iodomethyl)‐4,5‐dihydro‐2 H ‐spiro[furan‐3,3′‐indolin]‐2′‐one. The optically active 3‐substituted‐3‐hydroxymethyl oxindoles and spiro‐oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.