Asymmetric Direct Vinylogous Michael Addition to 2‑Enoylpyridine N‑Oxides Catalyzed by Bifunctional Thio-Urea

Catalytic enantioselective direct vinylogous Michael addition of α,α-dicyanoalkenes to 2-enoylpyridine N-oxides with a bifunctional organocatalyst is described. The methodology offers an efficient way to install an asymmetric carbon–carbon bond at the γ-position of α,α-dicyanoalkenes in excellent re...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2014-11, Vol.16 (21), p.5568-5571
Hauptverfasser:	Rout, Subhrajit, Ray, Sumit K, Unhale, Rajshekhar A, Singh, Vinod K
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Molecular Structure Nitriles - chemistry Pyridines - chemistry Stereoisomerism Thiourea - chemistry
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	5571
container_issue	21
container_start_page	5568
container_title	Organic letters
container_volume	16
creator	Rout, Subhrajit Ray, Sumit K Unhale, Rajshekhar A Singh, Vinod K
description	Catalytic enantioselective direct vinylogous Michael addition of α,α-dicyanoalkenes to 2-enoylpyridine N-oxides with a bifunctional organocatalyst is described. The methodology offers an efficient way to install an asymmetric carbon–carbon bond at the γ-position of α,α-dicyanoalkenes in excellent regio-, diastereo-, and enantioselectivity. Further, application in desymmetrization of achiral α,α-dicyanoalkene to access highly functionalized enantioenriched cyclohexylidenemalononitrile derivatives has been demonstrated.
doi_str_mv	10.1021/ol5025794
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1622064456</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1622064456</sourcerecordid><originalsourceid>FETCH-LOGICAL-a315t-b2a828b29fa405af335ce7738e158d35103e5ecc3052cb480da8c52b0ee2d2f23</originalsourceid><addsrcrecordid>eNptkMtOwzAURC0EolBY8APIGyRYBPyIk3RZSnlIPDYt28ixb6iRExc7kQgrfoFf5EtIVeiK1b0anRlpBqEjSs4pYfTCWUGYSEfxFtqjgvEoJYJtb_6EDNB-CK-E0F4Z7aIBE5ykNEn30Ns4dFUFjTcKXxkPqsHPpu6se3FtwA9GLSRYPNbaNMbVuHGYfX9-TWvX2WXnjTY14MdeeXo3GgKeyEba7gM0Ljp8acq2ViuftHi2MC6ae5AHaKeUNsDh7x2i-fV0NrmN7p9u7ibj-0hyKpqoYDJjWcFGpYyJkCXnQkGa8gyoyDQXlHAQoBTvq6oizoiWmRKsIABMs5LxITpd5y69e2shNHllggJrZQ19t5wmjJEkjkXSo2drVHkXgocyX3pTSd_llOSrhfPNwj17_BvbFhXoDfk3aQ-crAGpQv7qWt-3D_8E_QBnx4RX</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1622064456</pqid></control><display><type>article</type><title>Asymmetric Direct Vinylogous Michael Addition to 2‑Enoylpyridine N‑Oxides Catalyzed by Bifunctional Thio-Urea</title><source>MEDLINE</source><source>ACS Publications</source><creator>Rout, Subhrajit ; Ray, Sumit K ; Unhale, Rajshekhar A ; Singh, Vinod K</creator><creatorcontrib>Rout, Subhrajit ; Ray, Sumit K ; Unhale, Rajshekhar A ; Singh, Vinod K</creatorcontrib><description>Catalytic enantioselective direct vinylogous Michael addition of α,α-dicyanoalkenes to 2-enoylpyridine N-oxides with a bifunctional organocatalyst is described. The methodology offers an efficient way to install an asymmetric carbon–carbon bond at the γ-position of α,α-dicyanoalkenes in excellent regio-, diastereo-, and enantioselectivity. Further, application in desymmetrization of achiral α,α-dicyanoalkene to access highly functionalized enantioenriched cyclohexylidenemalononitrile derivatives has been demonstrated.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol5025794</identifier><identifier>PMID: 25307167</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; Molecular Structure ; Nitriles - chemistry ; Pyridines - chemistry ; Stereoisomerism ; Thiourea - chemistry</subject><ispartof>Organic letters, 2014-11, Vol.16 (21), p.5568-5571</ispartof><rights>Copyright © 2014 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-b2a828b29fa405af335ce7738e158d35103e5ecc3052cb480da8c52b0ee2d2f23</citedby><cites>FETCH-LOGICAL-a315t-b2a828b29fa405af335ce7738e158d35103e5ecc3052cb480da8c52b0ee2d2f23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol5025794$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol5025794$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25307167$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rout, Subhrajit</creatorcontrib><creatorcontrib>Ray, Sumit K</creatorcontrib><creatorcontrib>Unhale, Rajshekhar A</creatorcontrib><creatorcontrib>Singh, Vinod K</creatorcontrib><title>Asymmetric Direct Vinylogous Michael Addition to 2‑Enoylpyridine N‑Oxides Catalyzed by Bifunctional Thio-Urea</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Catalytic enantioselective direct vinylogous Michael addition of α,α-dicyanoalkenes to 2-enoylpyridine N-oxides with a bifunctional organocatalyst is described. The methodology offers an efficient way to install an asymmetric carbon–carbon bond at the γ-position of α,α-dicyanoalkenes in excellent regio-, diastereo-, and enantioselectivity. Further, application in desymmetrization of achiral α,α-dicyanoalkene to access highly functionalized enantioenriched cyclohexylidenemalononitrile derivatives has been demonstrated.</description><subject>Catalysis</subject><subject>Molecular Structure</subject><subject>Nitriles - chemistry</subject><subject>Pyridines - chemistry</subject><subject>Stereoisomerism</subject><subject>Thiourea - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOwzAURC0EolBY8APIGyRYBPyIk3RZSnlIPDYt28ixb6iRExc7kQgrfoFf5EtIVeiK1b0anRlpBqEjSs4pYfTCWUGYSEfxFtqjgvEoJYJtb_6EDNB-CK-E0F4Z7aIBE5ykNEn30Ns4dFUFjTcKXxkPqsHPpu6se3FtwA9GLSRYPNbaNMbVuHGYfX9-TWvX2WXnjTY14MdeeXo3GgKeyEba7gM0Ljp8acq2ViuftHi2MC6ae5AHaKeUNsDh7x2i-fV0NrmN7p9u7ibj-0hyKpqoYDJjWcFGpYyJkCXnQkGa8gyoyDQXlHAQoBTvq6oizoiWmRKsIABMs5LxITpd5y69e2shNHllggJrZQ19t5wmjJEkjkXSo2drVHkXgocyX3pTSd_llOSrhfPNwj17_BvbFhXoDfk3aQ-crAGpQv7qWt-3D_8E_QBnx4RX</recordid><startdate>20141107</startdate><enddate>20141107</enddate><creator>Rout, Subhrajit</creator><creator>Ray, Sumit K</creator><creator>Unhale, Rajshekhar A</creator><creator>Singh, Vinod K</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20141107</creationdate><title>Asymmetric Direct Vinylogous Michael Addition to 2‑Enoylpyridine N‑Oxides Catalyzed by Bifunctional Thio-Urea</title><author>Rout, Subhrajit ; Ray, Sumit K ; Unhale, Rajshekhar A ; Singh, Vinod K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-b2a828b29fa405af335ce7738e158d35103e5ecc3052cb480da8c52b0ee2d2f23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Catalysis</topic><topic>Molecular Structure</topic><topic>Nitriles - chemistry</topic><topic>Pyridines - chemistry</topic><topic>Stereoisomerism</topic><topic>Thiourea - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rout, Subhrajit</creatorcontrib><creatorcontrib>Ray, Sumit K</creatorcontrib><creatorcontrib>Unhale, Rajshekhar A</creatorcontrib><creatorcontrib>Singh, Vinod K</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><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>Ray, Sumit K</au><au>Unhale, Rajshekhar A</au><au>Singh, Vinod K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Direct Vinylogous Michael Addition to 2‑Enoylpyridine N‑Oxides Catalyzed by Bifunctional Thio-Urea</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2014-11-07</date><risdate>2014</risdate><volume>16</volume><issue>21</issue><spage>5568</spage><epage>5571</epage><pages>5568-5571</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Catalytic enantioselective direct vinylogous Michael addition of α,α-dicyanoalkenes to 2-enoylpyridine N-oxides with a bifunctional organocatalyst is described. The methodology offers an efficient way to install an asymmetric carbon–carbon bond at the γ-position of α,α-dicyanoalkenes in excellent regio-, diastereo-, and enantioselectivity. Further, application in desymmetrization of achiral α,α-dicyanoalkene to access highly functionalized enantioenriched cyclohexylidenemalononitrile derivatives has been demonstrated.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25307167</pmid><doi>10.1021/ol5025794</doi><tpages>4</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 1523-7060
ispartof	Organic letters, 2014-11, Vol.16 (21), p.5568-5571
issn	1523-7060 1523-7052
language	eng
recordid	cdi_proquest_miscellaneous_1622064456
source	MEDLINE; ACS Publications
subjects	Catalysis Molecular Structure Nitriles - chemistry Pyridines - chemistry Stereoisomerism Thiourea - chemistry
title	Asymmetric Direct Vinylogous Michael Addition to 2‑Enoylpyridine N‑Oxides Catalyzed by Bifunctional Thio-Urea
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T21%3A25%3A38IST&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%20Direct%20Vinylogous%20Michael%20Addition%20to%202%E2%80%91Enoylpyridine%20N%E2%80%91Oxides%20Catalyzed%20by%20Bifunctional%20Thio-Urea&rft.jtitle=Organic%20letters&rft.au=Rout,%20Subhrajit&rft.date=2014-11-07&rft.volume=16&rft.issue=21&rft.spage=5568&rft.epage=5571&rft.pages=5568-5571&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol5025794&rft_dat=%3Cproquest_cross%3E1622064456%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=1622064456&rft_id=info:pmid/25307167&rfr_iscdi=true