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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crwiley:10.1002/chir.23284 2024-06-02T07:58:06+00:00 Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles Kumar, Naveen Kumar, Akshay Sahoo, Subash Chandra Chimni, Swapandeep Singh Council of Scientific and Industrial Research, India 2020 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 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Chirality volume 32, issue 12, page 1377-1394 ISSN 0899-0042 1520-636X journal-article 2020 crwiley https://doi.org/10.1002/chir.23284 2024-05-03T10:47:23Z 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. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Spiro ENVELOPE(-59.000,-59.000,-62.267,-62.267) Chirality 32 12 1377 1394 |
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Wiley Online Library |
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description |
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. |
author2 |
Council of Scientific and Industrial Research, India |
format |
Article in Journal/Newspaper |
author |
Kumar, Naveen Kumar, Akshay Sahoo, Subash Chandra Chimni, Swapandeep Singh |
spellingShingle |
Kumar, Naveen Kumar, Akshay Sahoo, Subash Chandra Chimni, Swapandeep Singh Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles |
author_facet |
Kumar, Naveen Kumar, Akshay Sahoo, Subash Chandra Chimni, Swapandeep Singh |
author_sort |
Kumar, Naveen |
title |
Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles |
title_short |
Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles |
title_full |
Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles |
title_fullStr |
Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles |
title_full_unstemmed |
Candida antarctica lipase‐B‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles |
title_sort |
candida antarctica lipase‐b‐catalyzed kinetic resolution of 1,3‐dialkyl‐3‐hydroxymethyl oxindoles |
publisher |
Wiley |
publishDate |
2020 |
url |
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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ENVELOPE(-59.000,-59.000,-62.267,-62.267) |
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Spiro |
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Spiro |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Chirality volume 32, issue 12, page 1377-1394 ISSN 0899-0042 1520-636X |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/chir.23284 |
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