Palladium-catalyzed enantioselective arylation of racemic ketones to form bridged bicycles via dynamic kinetic resolution

Palladium-catalyzed enantioselective arylation of racemic ketones to form bridged bicycles via dynamic kinetic resolution

Enantioselective α‐arylation of racemic ketones containing existing α′‐stereocenters is reported for the first time via base‐induced dynamic kinetic resolution. Bridged bicyclic rings are formed in good ee values, which are difficult to obtain otherwise. Furthermore, reactions in DMSO‐d6 resulted in...

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Main Authors: Huang, Xiaolei, Oh, William Ray Jun Jie, Zhou, Steve Jianrong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2019
Subjects:
Alkylation
DRNTU::Science::Chemistry
Palladium Catalysis
Online Access:https://hdl.handle.net/10356/86101
http://hdl.handle.net/10220/48295
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-861012023-02-28T19:22:17Z Palladium-catalyzed enantioselective arylation of racemic ketones to form bridged bicycles via dynamic kinetic resolution Huang, Xiaolei Oh, William Ray Jun Jie Zhou, Steve Jianrong School of Physical and Mathematical Sciences Alkylation DRNTU::Science::Chemistry Palladium Catalysis Enantioselective α‐arylation of racemic ketones containing existing α′‐stereocenters is reported for the first time via base‐induced dynamic kinetic resolution. Bridged bicyclic rings are formed in good ee values, which are difficult to obtain otherwise. Furthermore, reactions in DMSO‐d6 resulted in extensive deuteration of both α‐ and α′‐positions in the products, thus supporting a pathway involving rapid, reversible deprotonation of ketones under catalytic conditions. MOE (Min. of Education, S’pore) Accepted version 2019-05-21T07:10:54Z 2019-12-06T16:16:02Z 2019-05-21T07:10:54Z 2019-12-06T16:16:02Z 2018 Journal Article Huang, X., Oh, W. R. J. J., & Zhou, S. J. (2018). Palladium-Catalyzed Enantioselective Arylation of Racemic Ketones to Form Bridged Bicycles via Dynamic Kinetic Resolution. Angewandte Chemie International Edition, 57(26), 7673-7677. doi:10.1002/anie.201804318 1433-7851 https://hdl.handle.net/10356/86101 http://hdl.handle.net/10220/48295 10.1002/anie.201804318 en Angewandte Chemie International Edition © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version of the following article: Huang, X., Oh, W. R. J. J., & Zhou, S. J. (2018). Palladium-Catalyzed Enantioselective Arylation of Racemic Ketones to Form Bridged Bicycles via Dynamic Kinetic Resolution. Angewandte Chemie International Edition, 57(26), 7673-7677, which has been published in final form at http://dx.doi.org/10.1002/anie.201804318. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. 5 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Alkylation
DRNTU::Science::Chemistry
Palladium Catalysis
spellingShingle Alkylation
DRNTU::Science::Chemistry
Palladium Catalysis
Huang, Xiaolei
Oh, William Ray Jun Jie
Zhou, Steve Jianrong
Palladium-catalyzed enantioselective arylation of racemic ketones to form bridged bicycles via dynamic kinetic resolution
description Enantioselective α‐arylation of racemic ketones containing existing α′‐stereocenters is reported for the first time via base‐induced dynamic kinetic resolution. Bridged bicyclic rings are formed in good ee values, which are difficult to obtain otherwise. Furthermore, reactions in DMSO‐d6 resulted in extensive deuteration of both α‐ and α′‐positions in the products, thus supporting a pathway involving rapid, reversible deprotonation of ketones under catalytic conditions.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Huang, Xiaolei
Oh, William Ray Jun Jie
Zhou, Steve Jianrong
format Article
author Huang, Xiaolei
Oh, William Ray Jun Jie
Zhou, Steve Jianrong
author_sort Huang, Xiaolei
title Palladium-catalyzed enantioselective arylation of racemic ketones to form bridged bicycles via dynamic kinetic resolution
title_short Palladium-catalyzed enantioselective arylation of racemic ketones to form bridged bicycles via dynamic kinetic resolution
title_full Palladium-catalyzed enantioselective arylation of racemic ketones to form bridged bicycles via dynamic kinetic resolution
title_fullStr Palladium-catalyzed enantioselective arylation of racemic ketones to form bridged bicycles via dynamic kinetic resolution
title_full_unstemmed Palladium-catalyzed enantioselective arylation of racemic ketones to form bridged bicycles via dynamic kinetic resolution
title_sort palladium-catalyzed enantioselective arylation of racemic ketones to form bridged bicycles via dynamic kinetic resolution
publishDate 2019
url https://hdl.handle.net/10356/86101
http://hdl.handle.net/10220/48295
_version_ 1759857728082149376

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