Anionic Diels–Alder Chemistry of Cyclic Sodium Dien-1-olates Delivering Highly Stereoselective and Functionalized Polycyclic Adducts

Anionic Diels–Alder chemistry of electron-deficient cross-conjugated vinylogous alkenones, providing highly stable sodium dienolate ion pairs as electron-rich dienes in the presence of a weak sodium base in THF, has been newly developed, leading to a single Diels–Alder adduct, in racemic form, in mo...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2021-08, Vol.23 (15), p.5709-5713
Main Authors: Huang, Jing-Kai, Shia, Kak-Shan
Format: Article
Language:English
Subjects:
Letter
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-a422t-c8909aa968e92e802fa4241268f0e8b92d9d3e47d0ae7ffe06d44c6ad195d0d93
cites cdi_FETCH-LOGICAL-a422t-c8909aa968e92e802fa4241268f0e8b92d9d3e47d0ae7ffe06d44c6ad195d0d93
container_end_page 5713
container_issue 15
container_start_page 5709
container_title Organic letters
container_volume 23
creator Huang, Jing-Kai
Shia, Kak-Shan
description Anionic Diels–Alder chemistry of electron-deficient cross-conjugated vinylogous alkenones, providing highly stable sodium dienolate ion pairs as electron-rich dienes in the presence of a weak sodium base in THF, has been newly developed, leading to a single Diels–Alder adduct, in racemic form, in moderate to high yields (up to 97%, 37 examples).
doi_str_mv 10.1021/acs.orglett.1c01807
format article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_8397436</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2554353839</sourcerecordid><originalsourceid>FETCH-LOGICAL-a422t-c8909aa968e92e802fa4241268f0e8b92d9d3e47d0ae7ffe06d44c6ad195d0d93</originalsourceid><addsrcrecordid>eNp9UUtqHDEQFSbGdpycIBsts-mxPv2RNoFhHNsBQwxO1kKWqmdkNJIjqQ2dVVa5gG-Yk0TDDIZssipVvU-Jegh9oGRBCaMX2uRFTGsPpSyoIVSQ4Qid0Y7xZiAde_P67skpepvzIyG0TuQJOuUtE7IX4gz9XgYXgzP40oHPf369LL2FhFcb2Lpc0ozjiFez8ZVxH62btjtiaGgTvS6Q8SV49wzJhTW-ceuNn_F9gQQxgwdTKoR1sPhqCrWJQXv3Eyy-i342e9OltZMp-R06HrXP8P5Qz9H3q8_fVjfN7dfrL6vlbaNbxkpjhCRS6_p1kAwEYWOdt5T1YiQgHiSz0nJoB0s0DOMIpLdta3ptqewssZKfo09736fpYQvWQChJe_WU3FanWUXt1L9IcBu1js9KcDm0vK8GHw8GKf6YIBdV72TAex0gTlmxrmt5xyu9UvmealLMOcH4uoYStUtQ1QTVIUF1SLCqLvaqHfgYp1SPlv-r-AtFvKWJ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2554353839</pqid></control><display><type>article</type><title>Anionic Diels–Alder Chemistry of Cyclic Sodium Dien-1-olates Delivering Highly Stereoselective and Functionalized Polycyclic Adducts</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Huang, Jing-Kai ; Shia, Kak-Shan</creator><creatorcontrib>Huang, Jing-Kai ; Shia, Kak-Shan</creatorcontrib><description>Anionic Diels–Alder chemistry of electron-deficient cross-conjugated vinylogous alkenones, providing highly stable sodium dienolate ion pairs as electron-rich dienes in the presence of a weak sodium base in THF, has been newly developed, leading to a single Diels–Alder adduct, in racemic form, in moderate to high yields (up to 97%, 37 examples).</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.1c01807</identifier><identifier>PMID: 34289688</identifier><language>eng</language><publisher>American Chemical Society</publisher><subject>Letter</subject><ispartof>Organic letters, 2021-08, Vol.23 (15), p.5709-5713</ispartof><rights>2021 The Authors. Published by American Chemical Society</rights><rights>2021 The Authors. Published by American Chemical Society 2021 The Authors</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a422t-c8909aa968e92e802fa4241268f0e8b92d9d3e47d0ae7ffe06d44c6ad195d0d93</citedby><cites>FETCH-LOGICAL-a422t-c8909aa968e92e802fa4241268f0e8b92d9d3e47d0ae7ffe06d44c6ad195d0d93</cites><orcidid>0000-0001-9560-2466</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids></links><search><creatorcontrib>Huang, Jing-Kai</creatorcontrib><creatorcontrib>Shia, Kak-Shan</creatorcontrib><title>Anionic Diels–Alder Chemistry of Cyclic Sodium Dien-1-olates Delivering Highly Stereoselective and Functionalized Polycyclic Adducts</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Anionic Diels–Alder chemistry of electron-deficient cross-conjugated vinylogous alkenones, providing highly stable sodium dienolate ion pairs as electron-rich dienes in the presence of a weak sodium base in THF, has been newly developed, leading to a single Diels–Alder adduct, in racemic form, in moderate to high yields (up to 97%, 37 examples).</description><subject>Letter</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9UUtqHDEQFSbGdpycIBsts-mxPv2RNoFhHNsBQwxO1kKWqmdkNJIjqQ2dVVa5gG-Yk0TDDIZssipVvU-Jegh9oGRBCaMX2uRFTGsPpSyoIVSQ4Qid0Y7xZiAde_P67skpepvzIyG0TuQJOuUtE7IX4gz9XgYXgzP40oHPf369LL2FhFcb2Lpc0ozjiFez8ZVxH62btjtiaGgTvS6Q8SV49wzJhTW-ceuNn_F9gQQxgwdTKoR1sPhqCrWJQXv3Eyy-i342e9OltZMp-R06HrXP8P5Qz9H3q8_fVjfN7dfrL6vlbaNbxkpjhCRS6_p1kAwEYWOdt5T1YiQgHiSz0nJoB0s0DOMIpLdta3ptqewssZKfo09736fpYQvWQChJe_WU3FanWUXt1L9IcBu1js9KcDm0vK8GHw8GKf6YIBdV72TAex0gTlmxrmt5xyu9UvmealLMOcH4uoYStUtQ1QTVIUF1SLCqLvaqHfgYp1SPlv-r-AtFvKWJ</recordid><startdate>20210806</startdate><enddate>20210806</enddate><creator>Huang, Jing-Kai</creator><creator>Shia, Kak-Shan</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-9560-2466</orcidid></search><sort><creationdate>20210806</creationdate><title>Anionic Diels–Alder Chemistry of Cyclic Sodium Dien-1-olates Delivering Highly Stereoselective and Functionalized Polycyclic Adducts</title><author>Huang, Jing-Kai ; Shia, Kak-Shan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a422t-c8909aa968e92e802fa4241268f0e8b92d9d3e47d0ae7ffe06d44c6ad195d0d93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Letter</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Jing-Kai</creatorcontrib><creatorcontrib>Shia, Kak-Shan</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huang, Jing-Kai</au><au>Shia, Kak-Shan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anionic Diels–Alder Chemistry of Cyclic Sodium Dien-1-olates Delivering Highly Stereoselective and Functionalized Polycyclic Adducts</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2021-08-06</date><risdate>2021</risdate><volume>23</volume><issue>15</issue><spage>5709</spage><epage>5713</epage><pages>5709-5713</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Anionic Diels–Alder chemistry of electron-deficient cross-conjugated vinylogous alkenones, providing highly stable sodium dienolate ion pairs as electron-rich dienes in the presence of a weak sodium base in THF, has been newly developed, leading to a single Diels–Alder adduct, in racemic form, in moderate to high yields (up to 97%, 37 examples).</abstract><pub>American Chemical Society</pub><pmid>34289688</pmid><doi>10.1021/acs.orglett.1c01807</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-9560-2466</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2021-08, Vol.23 (15), p.5709-5713
issn 1523-7060
1523-7052
language eng
recordid cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_8397436
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Letter
title Anionic Diels–Alder Chemistry of Cyclic Sodium Dien-1-olates Delivering Highly Stereoselective and Functionalized Polycyclic Adducts
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T11%3A07%3A39IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Anionic%20Diels%E2%80%93Alder%20Chemistry%20of%20Cyclic%20Sodium%20Dien-1-olates%20Delivering%20Highly%20Stereoselective%20and%20Functionalized%20Polycyclic%20Adducts&rft.jtitle=Organic%20letters&rft.au=Huang,%20Jing-Kai&rft.date=2021-08-06&rft.volume=23&rft.issue=15&rft.spage=5709&rft.epage=5713&rft.pages=5709-5713&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.1c01807&rft_dat=%3Cproquest_pubme%3E2554353839%3C/proquest_pubme%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a422t-c8909aa968e92e802fa4241268f0e8b92d9d3e47d0ae7ffe06d44c6ad195d0d93%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2554353839&rft_id=info:pmid/34289688&rfr_iscdi=true