N‑Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β‑Hydroxylation of Enals

N‑Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β‑Hydroxylation of Enals

An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl...

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Main Authors: Zhang, Yuexia, Du, Yu, Huang, Zhijian, Xu, Jianfeng, Wu, Xingxing, Wang, Yuhuang, Wang, Ming, Yang, Song, Webster, Richard D., Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2016
Subjects:
Chemistry and Biological Chemistry
Online Access:https://hdl.handle.net/10356/80814
http://hdl.handle.net/10220/40626
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-808142020-03-07T12:31:27Z N‑Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β‑Hydroxylation of Enals Zhang, Yuexia Du, Yu Huang, Zhijian Xu, Jianfeng Wu, Xingxing Wang, Yuhuang Wang, Ming Yang, Song Webster, Richard D. Chi, Robin Yonggui School of Physical and Mathematical Sciences Chemistry and Biological Chemistry An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules. NRF (Natl Research Foundation, S’pore) 2016-06-07T05:59:29Z 2019-12-06T13:59:31Z 2016-06-07T05:59:29Z 2019-12-06T13:59:31Z 2015 2015 Journal Article Zhang, Y., Du, Y., Huang, Z., Xu, J., Wu, X., Wang, Y., et al. (2015). N-Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β-Hydroxylation of Enals. Journal of the American Chemical Society, 137(7), 2416-2419. 0002-7863 https://hdl.handle.net/10356/80814 http://hdl.handle.net/10220/40626 10.1021/ja511371a 184173 en Journal of the American Chemical Society © 2015 American Chemical Society (ACS). 4 p.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic Chemistry and Biological Chemistry
spellingShingle Chemistry and Biological Chemistry
Zhang, Yuexia
Du, Yu
Huang, Zhijian
Xu, Jianfeng
Wu, Xingxing
Wang, Yuhuang
Wang, Ming
Yang, Song
Webster, Richard D.
Chi, Robin Yonggui
N‑Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β‑Hydroxylation of Enals
description An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Zhang, Yuexia
Du, Yu
Huang, Zhijian
Xu, Jianfeng
Wu, Xingxing
Wang, Yuhuang
Wang, Ming
Yang, Song
Webster, Richard D.
Chi, Robin Yonggui
format Article
author Zhang, Yuexia
Du, Yu
Huang, Zhijian
Xu, Jianfeng
Wu, Xingxing
Wang, Yuhuang
Wang, Ming
Yang, Song
Webster, Richard D.
Chi, Robin Yonggui
author_sort Zhang, Yuexia
title N‑Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β‑Hydroxylation of Enals
title_short N‑Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β‑Hydroxylation of Enals
title_full N‑Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β‑Hydroxylation of Enals
title_fullStr N‑Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β‑Hydroxylation of Enals
title_full_unstemmed N‑Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β‑Hydroxylation of Enals
title_sort n‑heterocyclic carbene-catalyzed radical reactions for highly enantioselective β‑hydroxylation of enals
publishDate 2016
url https://hdl.handle.net/10356/80814
http://hdl.handle.net/10220/40626
_version_ 1681040693483536384

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