Organometallic Reactions in Aqueous Media. Indium- and Zinc-Mediated Allylation of Sulfonimines1

Sulfonimines derived from aryl and nonenolizable aliphatic aldehydes can be effectively allylated to the corresponding homoallylic sulfonamides with allylic bromides promoted by indium or zinc. The solvent used can be water, THF, or a mixed aqueous THF solvent. The regioselectivity and stereoselecti...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2000-12, Vol.65 (25), p.8589-8594
Hauptverfasser: Lu, Wenshuo, Chan, Tak Hang
Format: Artikel
Sprache:eng ; jpn
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 8594
container_issue 25
container_start_page 8589
container_title Journal of organic chemistry
container_volume 65
creator Lu, Wenshuo
Chan, Tak Hang
description Sulfonimines derived from aryl and nonenolizable aliphatic aldehydes can be effectively allylated to the corresponding homoallylic sulfonamides with allylic bromides promoted by indium or zinc. The solvent used can be water, THF, or a mixed aqueous THF solvent. The regioselectivity and stereoselectivity of the reaction were studied.
doi_str_mv 10.1021/jo0009898
format Article
fullrecord <record><control><sourceid>acs_istex</sourceid><recordid>TN_cdi_istex_primary_ark_67375_TPS_FM8X3VCZ_S</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>a33544019</sourcerecordid><originalsourceid>FETCH-LOGICAL-a1340-61826b1857b4180a18c61d6a8ded4e984eda4376439f23d8b2478f8973830a723</originalsourceid><addsrcrecordid>eNo9kM9LwzAcxYMoOKcH_4NcPHbmV5P0OIbTwcbETZFd4ndNKpltqk0L7r-3c-LpwePzHo-H0DUlI0oYvd3VhJBMZ_oEDWjKSCIzIk7RgBDGEs4kP0cXMe56iKRpOkBvy-YdQl25FsrS5_jJQd76OkTsAx5_da7uIl4462GEZ8H6rkowBIs3PuTJr986i8dluS_hkMN1gVddWdTBVz64SC_RWQFldFd_OkTP07v15CGZL-9nk_E8AcpFP5NqJrdUp2orqCZAdS6plaCts8JlWjgLgispeFYwbvWWCaULnSmuOQHF-BAlx14fW_dtPhtfQbM30HwYqbhKzfpxZaYL_cpfJhuz6vmbIw95NLu6a0K_zlBiDjea_xv5D3YQYv8</addsrcrecordid><sourcetype>Publisher</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Organometallic Reactions in Aqueous Media. Indium- and Zinc-Mediated Allylation of Sulfonimines1</title><source>ACS Publications</source><creator>Lu, Wenshuo ; Chan, Tak Hang</creator><creatorcontrib>Lu, Wenshuo ; Chan, Tak Hang</creatorcontrib><description>Sulfonimines derived from aryl and nonenolizable aliphatic aldehydes can be effectively allylated to the corresponding homoallylic sulfonamides with allylic bromides promoted by indium or zinc. The solvent used can be water, THF, or a mixed aqueous THF solvent. The regioselectivity and stereoselectivity of the reaction were studied.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0009898</identifier><language>eng ; jpn</language><publisher>American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2000-12, Vol.65 (25), p.8589-8594</ispartof><rights>Copyright © 2000 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo0009898$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo0009898$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,27074,27922,27923,56736,56786</link.rule.ids></links><search><creatorcontrib>Lu, Wenshuo</creatorcontrib><creatorcontrib>Chan, Tak Hang</creatorcontrib><title>Organometallic Reactions in Aqueous Media. Indium- and Zinc-Mediated Allylation of Sulfonimines1</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Sulfonimines derived from aryl and nonenolizable aliphatic aldehydes can be effectively allylated to the corresponding homoallylic sulfonamides with allylic bromides promoted by indium or zinc. The solvent used can be water, THF, or a mixed aqueous THF solvent. The regioselectivity and stereoselectivity of the reaction were studied.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNo9kM9LwzAcxYMoOKcH_4NcPHbmV5P0OIbTwcbETZFd4ndNKpltqk0L7r-3c-LpwePzHo-H0DUlI0oYvd3VhJBMZ_oEDWjKSCIzIk7RgBDGEs4kP0cXMe56iKRpOkBvy-YdQl25FsrS5_jJQd76OkTsAx5_da7uIl4462GEZ8H6rkowBIs3PuTJr986i8dluS_hkMN1gVddWdTBVz64SC_RWQFldFd_OkTP07v15CGZL-9nk_E8AcpFP5NqJrdUp2orqCZAdS6plaCts8JlWjgLgispeFYwbvWWCaULnSmuOQHF-BAlx14fW_dtPhtfQbM30HwYqbhKzfpxZaYL_cpfJhuz6vmbIw95NLu6a0K_zlBiDjea_xv5D3YQYv8</recordid><startdate>20001215</startdate><enddate>20001215</enddate><creator>Lu, Wenshuo</creator><creator>Chan, Tak Hang</creator><general>American Chemical Society</general><scope>BSCLL</scope></search><sort><creationdate>20001215</creationdate><title>Organometallic Reactions in Aqueous Media. Indium- and Zinc-Mediated Allylation of Sulfonimines1</title><author>Lu, Wenshuo ; Chan, Tak Hang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a1340-61826b1857b4180a18c61d6a8ded4e984eda4376439f23d8b2478f8973830a723</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng ; jpn</language><creationdate>2000</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lu, Wenshuo</creatorcontrib><creatorcontrib>Chan, Tak Hang</creatorcontrib><collection>Istex</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lu, Wenshuo</au><au>Chan, Tak Hang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Organometallic Reactions in Aqueous Media. Indium- and Zinc-Mediated Allylation of Sulfonimines1</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2000-12-15</date><risdate>2000</risdate><volume>65</volume><issue>25</issue><spage>8589</spage><epage>8594</epage><pages>8589-8594</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Sulfonimines derived from aryl and nonenolizable aliphatic aldehydes can be effectively allylated to the corresponding homoallylic sulfonamides with allylic bromides promoted by indium or zinc. The solvent used can be water, THF, or a mixed aqueous THF solvent. The regioselectivity and stereoselectivity of the reaction were studied.</abstract><pub>American Chemical Society</pub><doi>10.1021/jo0009898</doi><tpages>6</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2000-12, Vol.65 (25), p.8589-8594
issn 0022-3263
1520-6904
language eng ; jpn
recordid cdi_istex_primary_ark_67375_TPS_FM8X3VCZ_S
source ACS Publications
title Organometallic Reactions in Aqueous Media. Indium- and Zinc-Mediated Allylation of Sulfonimines1
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T13%3A24%3A05IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_istex&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Organometallic%20Reactions%20in%20Aqueous%20Media.%20Indium-%20and%20Zinc-Mediated%20Allylation%20of%20Sulfonimines1&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Lu,%20Wenshuo&rft.date=2000-12-15&rft.volume=65&rft.issue=25&rft.spage=8589&rft.epage=8594&rft.pages=8589-8594&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/jo0009898&rft_dat=%3Cacs_istex%3Ea33544019%3C/acs_istex%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true