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

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...

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Bibliographic Details
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
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Summary: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.

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