Loading…
TEMPO-Enabled Electrochemical Enantioselective Oxidative Coupling of Secondary Acyclic Amines with Ketones
An electrochemical asymmetric coupling of secondary acyclic amines with ketones via a Shono-type oxidation has been described, affording the corresponding amino acid derivatives with good to excellent diastereoselectivity and enantioselectivity. The addition of an N-oxyl radical as a redox mediator...
Saved in:
Published in: | Journal of the American Chemical Society 2021-09, Vol.143 (38), p.15599-15605 |
---|---|
Main Authors: | , , , , , , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | cdi_FETCH-LOGICAL-a324t-e7dd56773921da529ddfd3f101b2f3949e13952036b42aae3b1c55d4bc34c2e03 |
---|---|
cites | cdi_FETCH-LOGICAL-a324t-e7dd56773921da529ddfd3f101b2f3949e13952036b42aae3b1c55d4bc34c2e03 |
container_end_page | 15605 |
container_issue | 38 |
container_start_page | 15599 |
container_title | Journal of the American Chemical Society |
container_volume | 143 |
creator | Wang, Zhen-Hua Gao, Pei-Sen Wang, Xiu Gao, Jun-Qing Xu, Xue-Tao He, Zeng Ma, Cong Mei, Tian-Sheng |
description | An electrochemical asymmetric coupling of secondary acyclic amines with ketones via a Shono-type oxidation has been described, affording the corresponding amino acid derivatives with good to excellent diastereoselectivity and enantioselectivity. The addition of an N-oxyl radical as a redox mediator could selectively oxidize the substrate rather than the product, although their oxidation potential difference is subtle (about 13 mV). This electrochemical transformation proceeds in the absence of stoichiometric additives, including metals, oxidants, and electrolytes, which gives it good functional group compatibility. Mechanistic studies suggest that proton-mediated racemization of the product is prevented by the reduction of protons at the cathode. |
doi_str_mv | 10.1021/jacs.1c08671 |
format | article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2574387152</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2574387152</sourcerecordid><originalsourceid>FETCH-LOGICAL-a324t-e7dd56773921da529ddfd3f101b2f3949e13952036b42aae3b1c55d4bc34c2e03</originalsourceid><addsrcrecordid>eNptkElPwzAQhS0EoqVw44x85ECKl6zHqgqLKCoS5Rw59oQ6SuISJ0D_PQ4tcOE0ntGbN34fQueUTClh9LoU0k6pJHEY0QM0pgEjXkBZeIjGhBDmRXHIR-jE2tK1PovpMRpxP-A88fkYlav08WnppY3IK1A4rUB2rZFrqLUUFXbzptPGwjDX74CXn1qJ79fc9JtKN6_YFPgZpGmUaLd4Jrey0hLPat2AxR-6W-MH6IxrTtFRISoLZ_s6QS836Wp-5y2Wt_fz2cITnPmdB5FSQRhFPGFUiYAlShWKF5TQnBXu0wlQnriQPMx9JgTwnMogUH4uuS8ZED5BlzvfTWveerBdVmsroapEA6a3GQsin8eRA-WkVzupbI21LRTZptW1y5FRkg10s4Futqfr5Bd75z6vQf2Kf3D-nR62StO3jQv6v9cX2ECDfg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2574387152</pqid></control><display><type>article</type><title>TEMPO-Enabled Electrochemical Enantioselective Oxidative Coupling of Secondary Acyclic Amines with Ketones</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)</source><creator>Wang, Zhen-Hua ; Gao, Pei-Sen ; Wang, Xiu ; Gao, Jun-Qing ; Xu, Xue-Tao ; He, Zeng ; Ma, Cong ; Mei, Tian-Sheng</creator><creatorcontrib>Wang, Zhen-Hua ; Gao, Pei-Sen ; Wang, Xiu ; Gao, Jun-Qing ; Xu, Xue-Tao ; He, Zeng ; Ma, Cong ; Mei, Tian-Sheng</creatorcontrib><description>An electrochemical asymmetric coupling of secondary acyclic amines with ketones via a Shono-type oxidation has been described, affording the corresponding amino acid derivatives with good to excellent diastereoselectivity and enantioselectivity. The addition of an N-oxyl radical as a redox mediator could selectively oxidize the substrate rather than the product, although their oxidation potential difference is subtle (about 13 mV). This electrochemical transformation proceeds in the absence of stoichiometric additives, including metals, oxidants, and electrolytes, which gives it good functional group compatibility. Mechanistic studies suggest that proton-mediated racemization of the product is prevented by the reduction of protons at the cathode.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.1c08671</identifier><identifier>PMID: 34533943</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of the American Chemical Society, 2021-09, Vol.143 (38), p.15599-15605</ispartof><rights>2021 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a324t-e7dd56773921da529ddfd3f101b2f3949e13952036b42aae3b1c55d4bc34c2e03</citedby><cites>FETCH-LOGICAL-a324t-e7dd56773921da529ddfd3f101b2f3949e13952036b42aae3b1c55d4bc34c2e03</cites><orcidid>0000-0001-7568-1347 ; 0000-0002-4985-1071</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34533943$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Zhen-Hua</creatorcontrib><creatorcontrib>Gao, Pei-Sen</creatorcontrib><creatorcontrib>Wang, Xiu</creatorcontrib><creatorcontrib>Gao, Jun-Qing</creatorcontrib><creatorcontrib>Xu, Xue-Tao</creatorcontrib><creatorcontrib>He, Zeng</creatorcontrib><creatorcontrib>Ma, Cong</creatorcontrib><creatorcontrib>Mei, Tian-Sheng</creatorcontrib><title>TEMPO-Enabled Electrochemical Enantioselective Oxidative Coupling of Secondary Acyclic Amines with Ketones</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>An electrochemical asymmetric coupling of secondary acyclic amines with ketones via a Shono-type oxidation has been described, affording the corresponding amino acid derivatives with good to excellent diastereoselectivity and enantioselectivity. The addition of an N-oxyl radical as a redox mediator could selectively oxidize the substrate rather than the product, although their oxidation potential difference is subtle (about 13 mV). This electrochemical transformation proceeds in the absence of stoichiometric additives, including metals, oxidants, and electrolytes, which gives it good functional group compatibility. Mechanistic studies suggest that proton-mediated racemization of the product is prevented by the reduction of protons at the cathode.</description><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNptkElPwzAQhS0EoqVw44x85ECKl6zHqgqLKCoS5Rw59oQ6SuISJ0D_PQ4tcOE0ntGbN34fQueUTClh9LoU0k6pJHEY0QM0pgEjXkBZeIjGhBDmRXHIR-jE2tK1PovpMRpxP-A88fkYlav08WnppY3IK1A4rUB2rZFrqLUUFXbzptPGwjDX74CXn1qJ79fc9JtKN6_YFPgZpGmUaLd4Jrey0hLPat2AxR-6W-MH6IxrTtFRISoLZ_s6QS836Wp-5y2Wt_fz2cITnPmdB5FSQRhFPGFUiYAlShWKF5TQnBXu0wlQnriQPMx9JgTwnMogUH4uuS8ZED5BlzvfTWveerBdVmsroapEA6a3GQsin8eRA-WkVzupbI21LRTZptW1y5FRkg10s4Futqfr5Bd75z6vQf2Kf3D-nR62StO3jQv6v9cX2ECDfg</recordid><startdate>20210929</startdate><enddate>20210929</enddate><creator>Wang, Zhen-Hua</creator><creator>Gao, Pei-Sen</creator><creator>Wang, Xiu</creator><creator>Gao, Jun-Qing</creator><creator>Xu, Xue-Tao</creator><creator>He, Zeng</creator><creator>Ma, Cong</creator><creator>Mei, Tian-Sheng</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7568-1347</orcidid><orcidid>https://orcid.org/0000-0002-4985-1071</orcidid></search><sort><creationdate>20210929</creationdate><title>TEMPO-Enabled Electrochemical Enantioselective Oxidative Coupling of Secondary Acyclic Amines with Ketones</title><author>Wang, Zhen-Hua ; Gao, Pei-Sen ; Wang, Xiu ; Gao, Jun-Qing ; Xu, Xue-Tao ; He, Zeng ; Ma, Cong ; Mei, Tian-Sheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a324t-e7dd56773921da529ddfd3f101b2f3949e13952036b42aae3b1c55d4bc34c2e03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Zhen-Hua</creatorcontrib><creatorcontrib>Gao, Pei-Sen</creatorcontrib><creatorcontrib>Wang, Xiu</creatorcontrib><creatorcontrib>Gao, Jun-Qing</creatorcontrib><creatorcontrib>Xu, Xue-Tao</creatorcontrib><creatorcontrib>He, Zeng</creatorcontrib><creatorcontrib>Ma, Cong</creatorcontrib><creatorcontrib>Mei, Tian-Sheng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Zhen-Hua</au><au>Gao, Pei-Sen</au><au>Wang, Xiu</au><au>Gao, Jun-Qing</au><au>Xu, Xue-Tao</au><au>He, Zeng</au><au>Ma, Cong</au><au>Mei, Tian-Sheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>TEMPO-Enabled Electrochemical Enantioselective Oxidative Coupling of Secondary Acyclic Amines with Ketones</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2021-09-29</date><risdate>2021</risdate><volume>143</volume><issue>38</issue><spage>15599</spage><epage>15605</epage><pages>15599-15605</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>An electrochemical asymmetric coupling of secondary acyclic amines with ketones via a Shono-type oxidation has been described, affording the corresponding amino acid derivatives with good to excellent diastereoselectivity and enantioselectivity. The addition of an N-oxyl radical as a redox mediator could selectively oxidize the substrate rather than the product, although their oxidation potential difference is subtle (about 13 mV). This electrochemical transformation proceeds in the absence of stoichiometric additives, including metals, oxidants, and electrolytes, which gives it good functional group compatibility. Mechanistic studies suggest that proton-mediated racemization of the product is prevented by the reduction of protons at the cathode.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>34533943</pmid><doi>10.1021/jacs.1c08671</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-7568-1347</orcidid><orcidid>https://orcid.org/0000-0002-4985-1071</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0002-7863 |
ispartof | Journal of the American Chemical Society, 2021-09, Vol.143 (38), p.15599-15605 |
issn | 0002-7863 1520-5126 |
language | eng |
recordid | cdi_proquest_miscellaneous_2574387152 |
source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
title | TEMPO-Enabled Electrochemical Enantioselective Oxidative Coupling of Secondary Acyclic Amines with Ketones |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-09-22T18%3A26%3A13IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=TEMPO-Enabled%20Electrochemical%20Enantioselective%20Oxidative%20Coupling%20of%20Secondary%20Acyclic%20Amines%20with%20Ketones&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Wang,%20Zhen-Hua&rft.date=2021-09-29&rft.volume=143&rft.issue=38&rft.spage=15599&rft.epage=15605&rft.pages=15599-15605&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/jacs.1c08671&rft_dat=%3Cproquest_cross%3E2574387152%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a324t-e7dd56773921da529ddfd3f101b2f3949e13952036b42aae3b1c55d4bc34c2e03%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2574387152&rft_id=info:pmid/34533943&rfr_iscdi=true |