Palladium-catalyzed one-pot highly regioselective 6-endo cyclization and alkylation of enynoates : synthesis of 2-alkanone pyrones

Palladium-catalyzed one-pot highly regioselective 6-endo cyclization and alkylation of enynoates : synthesis of 2-alkanone pyrones

The Pd(II)-catalyzed one-pot tandem cyclization/alkylation reactions of enynoates with allylic alcohols have been demonstrated. In this reaction, an innovative protocol proceeded well through Pd-catalyzed intramolecular selective 6- endo cyclization, insertion of allylic alcohols into the Pd-C bond...

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Main Authors: Tanveer Ahmad, Qiu, Sheng-Qi, Xu, Yun-He, Loh, Teck-Peng
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry
Alcohols
Cyclization
Online Access:https://hdl.handle.net/10356/139335
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1393352020-05-19T02:38:48Z Palladium-catalyzed one-pot highly regioselective 6-endo cyclization and alkylation of enynoates : synthesis of 2-alkanone pyrones Tanveer Ahmad Qiu, Sheng-Qi Xu, Yun-He Loh, Teck-Peng School of Physical and Mathematical Sciences Science::Chemistry Alcohols Cyclization The Pd(II)-catalyzed one-pot tandem cyclization/alkylation reactions of enynoates with allylic alcohols have been demonstrated. In this reaction, an innovative protocol proceeded well through Pd-catalyzed intramolecular selective 6- endo cyclization, insertion of allylic alcohols into the Pd-C bond of vinylpalladium species generated in situ, and β-hydrogen elimination processes. This conversion provides a convenient and efficient methodology for the synthesis of 2-alkanone pyrones in moderate to good yields. 2020-05-19T02:38:48Z 2020-05-19T02:38:48Z 2018 Journal Article Tanveer Ahmad, Qiu, S.-Q., Xu, Y.-H., & Loh, T.-P. (2018). Palladium-catalyzed one-pot highly regioselective 6-endo cyclization and alkylation of enynoates : synthesis of 2-alkanone pyrones. The Journal of Organic Chemistry, 83(21), 13414-13426. doi:10.1021/acs.joc.8b02198 0022-3263 https://hdl.handle.net/10356/139335 10.1021/acs.joc.8b02198 30354107 2-s2.0-85055689248 21 83 13414 13426 en The Journal of Organic Chemistry © 2018 American Chemical Society. All rights reserved.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic Science::Chemistry
Alcohols
Cyclization
spellingShingle Science::Chemistry
Alcohols
Cyclization
Tanveer Ahmad
Qiu, Sheng-Qi
Xu, Yun-He
Loh, Teck-Peng
Palladium-catalyzed one-pot highly regioselective 6-endo cyclization and alkylation of enynoates : synthesis of 2-alkanone pyrones
description The Pd(II)-catalyzed one-pot tandem cyclization/alkylation reactions of enynoates with allylic alcohols have been demonstrated. In this reaction, an innovative protocol proceeded well through Pd-catalyzed intramolecular selective 6- endo cyclization, insertion of allylic alcohols into the Pd-C bond of vinylpalladium species generated in situ, and β-hydrogen elimination processes. This conversion provides a convenient and efficient methodology for the synthesis of 2-alkanone pyrones in moderate to good yields.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Tanveer Ahmad
Qiu, Sheng-Qi
Xu, Yun-He
Loh, Teck-Peng
format Article
author Tanveer Ahmad
Qiu, Sheng-Qi
Xu, Yun-He
Loh, Teck-Peng
author_sort Tanveer Ahmad
title Palladium-catalyzed one-pot highly regioselective 6-endo cyclization and alkylation of enynoates : synthesis of 2-alkanone pyrones
title_short Palladium-catalyzed one-pot highly regioselective 6-endo cyclization and alkylation of enynoates : synthesis of 2-alkanone pyrones
title_full Palladium-catalyzed one-pot highly regioselective 6-endo cyclization and alkylation of enynoates : synthesis of 2-alkanone pyrones
title_fullStr Palladium-catalyzed one-pot highly regioselective 6-endo cyclization and alkylation of enynoates : synthesis of 2-alkanone pyrones
title_full_unstemmed Palladium-catalyzed one-pot highly regioselective 6-endo cyclization and alkylation of enynoates : synthesis of 2-alkanone pyrones
title_sort palladium-catalyzed one-pot highly regioselective 6-endo cyclization and alkylation of enynoates : synthesis of 2-alkanone pyrones
publishDate 2020
url https://hdl.handle.net/10356/139335
_version_ 1681056960197165056

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