α‑Alkylation of Chiral Sulfinimines for Constructing Quaternary Chiral Carbons by Introducing Removable Directing Groups

This study developed a facile and efficient synthetic strategy to construct quaternary chiral centers at the α-position of imines and ketones. High regioselectivity and diastereoselectivity were achieved through the synergetic effect of electron-withdrawing directing groups and N-tert-butyl sulfinam...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2018-03, Vol.20 (5), p.1350-1354
Hauptverfasser: Qin, Shuanglin, Liu, Shuangwei, Cao, Yuting, Li, Jiangnan, Chong, Chuanke, Liu, Tongtong, Luo, Yunhao, Hu, Jiyun, Jiang, Shende, Zhou, Honggang, Yang, Guang, Yang, Cheng
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1354
container_issue 5
container_start_page 1350
container_title Organic letters
container_volume 20
creator Qin, Shuanglin
Liu, Shuangwei
Cao, Yuting
Li, Jiangnan
Chong, Chuanke
Liu, Tongtong
Luo, Yunhao
Hu, Jiyun
Jiang, Shende
Zhou, Honggang
Yang, Guang
Yang, Cheng
description This study developed a facile and efficient synthetic strategy to construct quaternary chiral centers at the α-position of imines and ketones. High regioselectivity and diastereoselectivity were achieved through the synergetic effect of electron-withdrawing directing groups and N-tert-butyl sulfinamide as chiral auxiliaries. Either of them could be removed under the optimized conditions without any epimerization.
doi_str_mv 10.1021/acs.orglett.8b00105
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2002484083</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2002484083</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-c7d0c11a0851eee077a9e6b02c53bdbdf7aeda7ffe276df03069e35bb7dc8a553</originalsourceid><addsrcrecordid>eNp9kEtuFDEQhi0EIiFwAiTkJZuZlNvtds8yaiBEioR4rVu2uxwc3O3BD6QRG67AUbgIh-AkeDSTLFlVqfT9VaqPkOcM1gwadq5MWod44zHnda8BGIgH5JSJhq8kiObhfd_BCXmS0m1F6mTzmJw0m7btOi5PyY8_v__-_HXhv-68yi4sNFg6fHFRefqxeOsWN7sFE7Uh0iEsKcdisltu6PuiMsZFxd0dP6ioK0H1jl4tOYapmD34AefwXWmP9JWLeAhfxlC26Sl5ZJVP-OxYz8jnN68_DW9X1-8ur4aL65XircgrIycwjCnoBUNEkFJtsNPQGMH1pCcrFU5KWouN7CYLHLoNcqG1nEyvhOBn5OVh7zaGbwVTHmeXDHqvFgwljQ1A0_Yt9Lyi_ICaGFKKaMdtdHN9cmQw7q2P1fp4tD4erdfUi-OBomec7jN3mitwfgD26dtQqjef_rvyH1QDlkA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2002484083</pqid></control><display><type>article</type><title>α‑Alkylation of Chiral Sulfinimines for Constructing Quaternary Chiral Carbons by Introducing Removable Directing Groups</title><source>ACS Publications</source><creator>Qin, Shuanglin ; Liu, Shuangwei ; Cao, Yuting ; Li, Jiangnan ; Chong, Chuanke ; Liu, Tongtong ; Luo, Yunhao ; Hu, Jiyun ; Jiang, Shende ; Zhou, Honggang ; Yang, Guang ; Yang, Cheng</creator><creatorcontrib>Qin, Shuanglin ; Liu, Shuangwei ; Cao, Yuting ; Li, Jiangnan ; Chong, Chuanke ; Liu, Tongtong ; Luo, Yunhao ; Hu, Jiyun ; Jiang, Shende ; Zhou, Honggang ; Yang, Guang ; Yang, Cheng</creatorcontrib><description>This study developed a facile and efficient synthetic strategy to construct quaternary chiral centers at the α-position of imines and ketones. High regioselectivity and diastereoselectivity were achieved through the synergetic effect of electron-withdrawing directing groups and N-tert-butyl sulfinamide as chiral auxiliaries. Either of them could be removed under the optimized conditions without any epimerization.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.8b00105</identifier><identifier>PMID: 29446637</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2018-03, Vol.20 (5), p.1350-1354</ispartof><rights>Copyright © 2018 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-c7d0c11a0851eee077a9e6b02c53bdbdf7aeda7ffe276df03069e35bb7dc8a553</citedby><cites>FETCH-LOGICAL-a345t-c7d0c11a0851eee077a9e6b02c53bdbdf7aeda7ffe276df03069e35bb7dc8a553</cites><orcidid>0000-0002-1773-9392</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.8b00105$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.8b00105$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29446637$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Qin, Shuanglin</creatorcontrib><creatorcontrib>Liu, Shuangwei</creatorcontrib><creatorcontrib>Cao, Yuting</creatorcontrib><creatorcontrib>Li, Jiangnan</creatorcontrib><creatorcontrib>Chong, Chuanke</creatorcontrib><creatorcontrib>Liu, Tongtong</creatorcontrib><creatorcontrib>Luo, Yunhao</creatorcontrib><creatorcontrib>Hu, Jiyun</creatorcontrib><creatorcontrib>Jiang, Shende</creatorcontrib><creatorcontrib>Zhou, Honggang</creatorcontrib><creatorcontrib>Yang, Guang</creatorcontrib><creatorcontrib>Yang, Cheng</creatorcontrib><title>α‑Alkylation of Chiral Sulfinimines for Constructing Quaternary Chiral Carbons by Introducing Removable Directing Groups</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>This study developed a facile and efficient synthetic strategy to construct quaternary chiral centers at the α-position of imines and ketones. High regioselectivity and diastereoselectivity were achieved through the synergetic effect of electron-withdrawing directing groups and N-tert-butyl sulfinamide as chiral auxiliaries. Either of them could be removed under the optimized conditions without any epimerization.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9kEtuFDEQhi0EIiFwAiTkJZuZlNvtds8yaiBEioR4rVu2uxwc3O3BD6QRG67AUbgIh-AkeDSTLFlVqfT9VaqPkOcM1gwadq5MWod44zHnda8BGIgH5JSJhq8kiObhfd_BCXmS0m1F6mTzmJw0m7btOi5PyY8_v__-_HXhv-68yi4sNFg6fHFRefqxeOsWN7sFE7Uh0iEsKcdisltu6PuiMsZFxd0dP6ioK0H1jl4tOYapmD34AefwXWmP9JWLeAhfxlC26Sl5ZJVP-OxYz8jnN68_DW9X1-8ur4aL65XircgrIycwjCnoBUNEkFJtsNPQGMH1pCcrFU5KWouN7CYLHLoNcqG1nEyvhOBn5OVh7zaGbwVTHmeXDHqvFgwljQ1A0_Yt9Lyi_ICaGFKKaMdtdHN9cmQw7q2P1fp4tD4erdfUi-OBomec7jN3mitwfgD26dtQqjef_rvyH1QDlkA</recordid><startdate>20180302</startdate><enddate>20180302</enddate><creator>Qin, Shuanglin</creator><creator>Liu, Shuangwei</creator><creator>Cao, Yuting</creator><creator>Li, Jiangnan</creator><creator>Chong, Chuanke</creator><creator>Liu, Tongtong</creator><creator>Luo, Yunhao</creator><creator>Hu, Jiyun</creator><creator>Jiang, Shende</creator><creator>Zhou, Honggang</creator><creator>Yang, Guang</creator><creator>Yang, Cheng</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1773-9392</orcidid></search><sort><creationdate>20180302</creationdate><title>α‑Alkylation of Chiral Sulfinimines for Constructing Quaternary Chiral Carbons by Introducing Removable Directing Groups</title><author>Qin, Shuanglin ; Liu, Shuangwei ; Cao, Yuting ; Li, Jiangnan ; Chong, Chuanke ; Liu, Tongtong ; Luo, Yunhao ; Hu, Jiyun ; Jiang, Shende ; Zhou, Honggang ; Yang, Guang ; Yang, Cheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-c7d0c11a0851eee077a9e6b02c53bdbdf7aeda7ffe276df03069e35bb7dc8a553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Qin, Shuanglin</creatorcontrib><creatorcontrib>Liu, Shuangwei</creatorcontrib><creatorcontrib>Cao, Yuting</creatorcontrib><creatorcontrib>Li, Jiangnan</creatorcontrib><creatorcontrib>Chong, Chuanke</creatorcontrib><creatorcontrib>Liu, Tongtong</creatorcontrib><creatorcontrib>Luo, Yunhao</creatorcontrib><creatorcontrib>Hu, Jiyun</creatorcontrib><creatorcontrib>Jiang, Shende</creatorcontrib><creatorcontrib>Zhou, Honggang</creatorcontrib><creatorcontrib>Yang, Guang</creatorcontrib><creatorcontrib>Yang, Cheng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Qin, Shuanglin</au><au>Liu, Shuangwei</au><au>Cao, Yuting</au><au>Li, Jiangnan</au><au>Chong, Chuanke</au><au>Liu, Tongtong</au><au>Luo, Yunhao</au><au>Hu, Jiyun</au><au>Jiang, Shende</au><au>Zhou, Honggang</au><au>Yang, Guang</au><au>Yang, Cheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>α‑Alkylation of Chiral Sulfinimines for Constructing Quaternary Chiral Carbons by Introducing Removable Directing Groups</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2018-03-02</date><risdate>2018</risdate><volume>20</volume><issue>5</issue><spage>1350</spage><epage>1354</epage><pages>1350-1354</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>This study developed a facile and efficient synthetic strategy to construct quaternary chiral centers at the α-position of imines and ketones. High regioselectivity and diastereoselectivity were achieved through the synergetic effect of electron-withdrawing directing groups and N-tert-butyl sulfinamide as chiral auxiliaries. Either of them could be removed under the optimized conditions without any epimerization.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>29446637</pmid><doi>10.1021/acs.orglett.8b00105</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-1773-9392</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2018-03, Vol.20 (5), p.1350-1354
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2002484083
source ACS Publications
title α‑Alkylation of Chiral Sulfinimines for Constructing Quaternary Chiral Carbons by Introducing Removable Directing Groups
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-14T19%3A05%3A45IST&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=%CE%B1%E2%80%91Alkylation%20of%20Chiral%20Sulfinimines%20for%20Constructing%20Quaternary%20Chiral%20Carbons%20by%20Introducing%20Removable%20Directing%20Groups&rft.jtitle=Organic%20letters&rft.au=Qin,%20Shuanglin&rft.date=2018-03-02&rft.volume=20&rft.issue=5&rft.spage=1350&rft.epage=1354&rft.pages=1350-1354&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.8b00105&rft_dat=%3Cproquest_cross%3E2002484083%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2002484083&rft_id=info:pmid/29446637&rfr_iscdi=true