Asymmetric Construction of Remote Vicinal Quaternary and Tertiary Stereocenters via Direct Doubly Vinylogous Michael Addition

Asymmetric Construction of Remote Vicinal Quaternary and Tertiary Stereocenters via Direct Doubly Vinylogous Michael Addition

An asymmetric direct doubly vinylogous Michael addition has been developed for the generation of sterically congested vicinal quaternary and tertiary stereocenters. This doubly vinylogous Michael addition of β,γ-unsaturated butenolides to 3-methyl-4-nitro-5-alkenyl isoxazoles, powered by a bifunctio...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2018-04, Vol.20 (8), p.2199-2203
Hauptverfasser: Rout, Subhrajit, Joshi, Harshit, Singh, Vinod K
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2203
container_issue 8
container_start_page 2199
container_title Organic letters
container_volume 20
creator Rout, Subhrajit
Joshi, Harshit
Singh, Vinod K
description An asymmetric direct doubly vinylogous Michael addition has been developed for the generation of sterically congested vicinal quaternary and tertiary stereocenters. This doubly vinylogous Michael addition of β,γ-unsaturated butenolides to 3-methyl-4-nitro-5-alkenyl isoxazoles, powered by a bifunctional squaramide, affords a broad range of densely functionalized enantioenriched γ,γ-disubstituted butenolides in high yields with excellent diastereo- and enantioselectivities in most cases. Moreover, the strategy highlights the first application of β,γ-unsaturated butenolides in an asymmetric 1,6-conjugate addition.
doi_str_mv 10.1021/acs.orglett.8b00493
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2019045175</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2019045175</sourcerecordid><originalsourceid>FETCH-LOGICAL-a411t-ef399ac6e8c4b96b9bbef059a054c06fc1d4b35c4760ab69b715f09e9435e7ef3</originalsourceid><addsrcrecordid>eNp9kMtOwzAQRS0E4v0FSMhLNi3jJE7qZVWeEgjx3Ea2MylGTgy2g9QF_46rli5ZjT26Z8Y-hJwwGDPI2LnUYez83GKM44kCKES-RfYZz_JRBTzb3pxL2CMHIXwAsNQRu2QvE3ySA8v3yc80LLoOozeazlwfoh90NK6nrqVP2LmI9M1o00tLHwcZ0ffSL6jsG_qCPprl5Tl10WnsUw3020h6YTzqSC_coOwi8f3CurkbAr03-l2ipdOmMcstR2SnlTbg8boektery5fZzeju4fp2Nr0byYKxOMI2F0LqEie6UKJUQilsgQsJvNBQtpo1hcq5LqoSpCqFqhhvQaAoco5Vog_J2Wrup3dfA4ZYdyZotFb2mN5VZ8AEFJxVPEXzVVR7F4LHtv70pkv_rBnUS-918l6vvddr74k6XS8YVIfNhvkTnQLnq8CS_nBD8mjDvyN_AeEalOk</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2019045175</pqid></control><display><type>article</type><title>Asymmetric Construction of Remote Vicinal Quaternary and Tertiary Stereocenters via Direct Doubly Vinylogous Michael Addition</title><source>ACS Publications</source><creator>Rout, Subhrajit ; Joshi, Harshit ; Singh, Vinod K</creator><creatorcontrib>Rout, Subhrajit ; Joshi, Harshit ; Singh, Vinod K</creatorcontrib><description>An asymmetric direct doubly vinylogous Michael addition has been developed for the generation of sterically congested vicinal quaternary and tertiary stereocenters. This doubly vinylogous Michael addition of β,γ-unsaturated butenolides to 3-methyl-4-nitro-5-alkenyl isoxazoles, powered by a bifunctional squaramide, affords a broad range of densely functionalized enantioenriched γ,γ-disubstituted butenolides in high yields with excellent diastereo- and enantioselectivities in most cases. Moreover, the strategy highlights the first application of β,γ-unsaturated butenolides in an asymmetric 1,6-conjugate addition.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.8b00493</identifier><identifier>PMID: 29583013</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2018-04, Vol.20 (8), p.2199-2203</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a411t-ef399ac6e8c4b96b9bbef059a054c06fc1d4b35c4760ab69b715f09e9435e7ef3</citedby><cites>FETCH-LOGICAL-a411t-ef399ac6e8c4b96b9bbef059a054c06fc1d4b35c4760ab69b715f09e9435e7ef3</cites><orcidid>0000-0003-0928-5543</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.8b00493$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.8b00493$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29583013$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rout, Subhrajit</creatorcontrib><creatorcontrib>Joshi, Harshit</creatorcontrib><creatorcontrib>Singh, Vinod K</creatorcontrib><title>Asymmetric Construction of Remote Vicinal Quaternary and Tertiary Stereocenters via Direct Doubly Vinylogous Michael Addition</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>An asymmetric direct doubly vinylogous Michael addition has been developed for the generation of sterically congested vicinal quaternary and tertiary stereocenters. This doubly vinylogous Michael addition of β,γ-unsaturated butenolides to 3-methyl-4-nitro-5-alkenyl isoxazoles, powered by a bifunctional squaramide, affords a broad range of densely functionalized enantioenriched γ,γ-disubstituted butenolides in high yields with excellent diastereo- and enantioselectivities in most cases. Moreover, the strategy highlights the first application of β,γ-unsaturated butenolides in an asymmetric 1,6-conjugate addition.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9kMtOwzAQRS0E4v0FSMhLNi3jJE7qZVWeEgjx3Ea2MylGTgy2g9QF_46rli5ZjT26Z8Y-hJwwGDPI2LnUYez83GKM44kCKES-RfYZz_JRBTzb3pxL2CMHIXwAsNQRu2QvE3ySA8v3yc80LLoOozeazlwfoh90NK6nrqVP2LmI9M1o00tLHwcZ0ffSL6jsG_qCPprl5Tl10WnsUw3020h6YTzqSC_coOwi8f3CurkbAr03-l2ipdOmMcstR2SnlTbg8boektery5fZzeju4fp2Nr0byYKxOMI2F0LqEie6UKJUQilsgQsJvNBQtpo1hcq5LqoSpCqFqhhvQaAoco5Vog_J2Wrup3dfA4ZYdyZotFb2mN5VZ8AEFJxVPEXzVVR7F4LHtv70pkv_rBnUS-918l6vvddr74k6XS8YVIfNhvkTnQLnq8CS_nBD8mjDvyN_AeEalOk</recordid><startdate>20180420</startdate><enddate>20180420</enddate><creator>Rout, Subhrajit</creator><creator>Joshi, Harshit</creator><creator>Singh, Vinod K</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-0928-5543</orcidid></search><sort><creationdate>20180420</creationdate><title>Asymmetric Construction of Remote Vicinal Quaternary and Tertiary Stereocenters via Direct Doubly Vinylogous Michael Addition</title><author>Rout, Subhrajit ; Joshi, Harshit ; Singh, Vinod K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a411t-ef399ac6e8c4b96b9bbef059a054c06fc1d4b35c4760ab69b715f09e9435e7ef3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rout, Subhrajit</creatorcontrib><creatorcontrib>Joshi, Harshit</creatorcontrib><creatorcontrib>Singh, Vinod K</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>Rout, Subhrajit</au><au>Joshi, Harshit</au><au>Singh, Vinod K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Construction of Remote Vicinal Quaternary and Tertiary Stereocenters via Direct Doubly Vinylogous Michael Addition</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2018-04-20</date><risdate>2018</risdate><volume>20</volume><issue>8</issue><spage>2199</spage><epage>2203</epage><pages>2199-2203</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>An asymmetric direct doubly vinylogous Michael addition has been developed for the generation of sterically congested vicinal quaternary and tertiary stereocenters. This doubly vinylogous Michael addition of β,γ-unsaturated butenolides to 3-methyl-4-nitro-5-alkenyl isoxazoles, powered by a bifunctional squaramide, affords a broad range of densely functionalized enantioenriched γ,γ-disubstituted butenolides in high yields with excellent diastereo- and enantioselectivities in most cases. Moreover, the strategy highlights the first application of β,γ-unsaturated butenolides in an asymmetric 1,6-conjugate addition.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>29583013</pmid><doi>10.1021/acs.orglett.8b00493</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-0928-5543</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2018-04, Vol.20 (8), p.2199-2203
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2019045175
source ACS Publications
title Asymmetric Construction of Remote Vicinal Quaternary and Tertiary Stereocenters via Direct Doubly Vinylogous Michael Addition
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-02T09%3A48%3A32IST&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=Asymmetric%20Construction%20of%20Remote%20Vicinal%20Quaternary%20and%20Tertiary%20Stereocenters%20via%20Direct%20Doubly%20Vinylogous%20Michael%20Addition&rft.jtitle=Organic%20letters&rft.au=Rout,%20Subhrajit&rft.date=2018-04-20&rft.volume=20&rft.issue=8&rft.spage=2199&rft.epage=2203&rft.pages=2199-2203&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.8b00493&rft_dat=%3Cproquest_cross%3E2019045175%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=2019045175&rft_id=info:pmid/29583013&rfr_iscdi=true