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...
Published in: | Chirality |
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Main Authors: | , , , |
Other Authors: | |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
2020
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Subjects: | |
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 |
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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