Organocatalytic Diastereodivergent Enantioselective Formal oxa‐Diels‐Alder Reaction of Unsaturated Ketones with Enoates Under Liquid‐Assisted Grinding Conditions
Chiral heterocycles occur in many compounds of interest, but their efficient synthesis is challenging. This study concerns the enantioselective and diastereoselective synthesis of densely substituted chiral pyran derivatives. Diastereodivergence of the oxa‐Diels‐Alder reaction is achieved by using e...
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| Veröffentlicht in: | ChemSusChem 2022-04, Vol.15 (7), p.e202200028-n/a |
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| creator | Peňaška, Tibor Modrocká, Viktória Stankovianska, Klára Mečiarová, Mária Rakovský, Erik Šebesta, Radovan |
| description | Chiral heterocycles occur in many compounds of interest, but their efficient synthesis is challenging. This study concerns the enantioselective and diastereoselective synthesis of densely substituted chiral pyran derivatives. Diastereodivergence of the oxa‐Diels‐Alder reaction is achieved by using either a bifunctional amino‐thiourea or a monofunctional quinine organocatalyst under ball‐milling conditions. Liquid‐assisted grinding proves a highly efficient means of affording pyrans in high yield, with high enantiomeric purities and short reaction times.
A LAG to stand on: Liquid‐assisted grinding (LAG) allows enantioselective and diastereodivergent construction of chiral pyran derivatives. The formal oxa‐Diels‐Alder reaction can be directed towards diastereomers by using either mono‐ or bifunctional organocatalysts. |
| doi_str_mv | 10.1002/cssc.202200028 |
| format | Article |
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A LAG to stand on: Liquid‐assisted grinding (LAG) allows enantioselective and diastereodivergent construction of chiral pyran derivatives. The formal oxa‐Diels‐Alder reaction can be directed towards diastereomers by using either mono‐ or bifunctional organocatalysts.</description><identifier>ISSN: 1864-5631</identifier><identifier>EISSN: 1864-564X</identifier><identifier>DOI: 10.1002/cssc.202200028</identifier><identifier>PMID: 35146952</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>asymmetric synthesis ; Catalysis ; Comminution ; Cycloaddition Reaction ; Diels-Alder reaction ; Enantiomers ; Grinding mills ; Ketones ; mechanochemistry ; O heterocycles ; organocatalysis ; Pyrans ; Stereoisomerism ; Stereoselectivity ; Synthesis</subject><ispartof>ChemSusChem, 2022-04, Vol.15 (7), p.e202200028-n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><rights>2022 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3738-fddea6876606ec39c98c883d9c34af834f40161c057b9f3c450f181a957842ab3</citedby><cites>FETCH-LOGICAL-c3738-fddea6876606ec39c98c883d9c34af834f40161c057b9f3c450f181a957842ab3</cites><orcidid>0000-0001-7017-5824 ; 0000-0002-6437-3223 ; 0000-0002-2249-7623 ; 0000-0003-1378-2972 ; 0000-0002-7975-3608 ; 0000-0001-6033-6073</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcssc.202200028$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcssc.202200028$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35146952$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Peňaška, Tibor</creatorcontrib><creatorcontrib>Modrocká, Viktória</creatorcontrib><creatorcontrib>Stankovianska, Klára</creatorcontrib><creatorcontrib>Mečiarová, Mária</creatorcontrib><creatorcontrib>Rakovský, Erik</creatorcontrib><creatorcontrib>Šebesta, Radovan</creatorcontrib><title>Organocatalytic Diastereodivergent Enantioselective Formal oxa‐Diels‐Alder Reaction of Unsaturated Ketones with Enoates Under Liquid‐Assisted Grinding Conditions</title><title>ChemSusChem</title><addtitle>ChemSusChem</addtitle><description>Chiral heterocycles occur in many compounds of interest, but their efficient synthesis is challenging. This study concerns the enantioselective and diastereoselective synthesis of densely substituted chiral pyran derivatives. Diastereodivergence of the oxa‐Diels‐Alder reaction is achieved by using either a bifunctional amino‐thiourea or a monofunctional quinine organocatalyst under ball‐milling conditions. Liquid‐assisted grinding proves a highly efficient means of affording pyrans in high yield, with high enantiomeric purities and short reaction times.
A LAG to stand on: Liquid‐assisted grinding (LAG) allows enantioselective and diastereodivergent construction of chiral pyran derivatives. The formal oxa‐Diels‐Alder reaction can be directed towards diastereomers by using either mono‐ or bifunctional organocatalysts.</description><subject>asymmetric synthesis</subject><subject>Catalysis</subject><subject>Comminution</subject><subject>Cycloaddition Reaction</subject><subject>Diels-Alder reaction</subject><subject>Enantiomers</subject><subject>Grinding mills</subject><subject>Ketones</subject><subject>mechanochemistry</subject><subject>O heterocycles</subject><subject>organocatalysis</subject><subject>Pyrans</subject><subject>Stereoisomerism</subject><subject>Stereoselectivity</subject><subject>Synthesis</subject><issn>1864-5631</issn><issn>1864-564X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkctu1DAUhiMEohfYskSW2LCZwY4dx1lW6QXESJUoldhFHvtkcJWxWx-HMjseoW_Be_VJ6mjaQeqG1W8ffeeT5b8o3jE6Z5SWnwyimZe0LGm-qRfFPlNSzCopfrzcnTnbKw4QryiVtJHydbHHKyZkU5X7xd_zuNI-GJ30sEnOkGOnMUGEYN0viCvwiZx47ZMLCAOYlKfkNMS1Hkj4re__3B07GDDn0WAhkm-gMxM8CT259KjTGHUCS75CCh6Q3Lr0MwtDHmIGppWFuxmdnQyIDif4LDpvnV-RNuScdPimeNXrAeHtYx4Wl6cn39vPs8X52Zf2aDEzvOZq1lsLWqpaSirB8MY0yijFbWO40L3ioheUSWZoVS-bnhtR0Z4pppuqVqLUS35YfNx6r2O4GQFTt3ZoYBi0hzBiV8pSlU3-OprRD8_QqzBGn1-XKVFLJmldZ2q-pUwMiBH67jq6tY6bjtFuqrCbKux2FeaF94_acbkGu8OfOstAswVu3QCb_-i69uKi_Sd_AGsxrqc</recordid><startdate>20220407</startdate><enddate>20220407</enddate><creator>Peňaška, Tibor</creator><creator>Modrocká, Viktória</creator><creator>Stankovianska, Klára</creator><creator>Mečiarová, Mária</creator><creator>Rakovský, Erik</creator><creator>Šebesta, Radovan</creator><general>Wiley Subscription Services, Inc</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7017-5824</orcidid><orcidid>https://orcid.org/0000-0002-6437-3223</orcidid><orcidid>https://orcid.org/0000-0002-2249-7623</orcidid><orcidid>https://orcid.org/0000-0003-1378-2972</orcidid><orcidid>https://orcid.org/0000-0002-7975-3608</orcidid><orcidid>https://orcid.org/0000-0001-6033-6073</orcidid></search><sort><creationdate>20220407</creationdate><title>Organocatalytic Diastereodivergent Enantioselective Formal oxa‐Diels‐Alder Reaction of Unsaturated Ketones with Enoates Under Liquid‐Assisted Grinding Conditions</title><author>Peňaška, Tibor ; 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This study concerns the enantioselective and diastereoselective synthesis of densely substituted chiral pyran derivatives. Diastereodivergence of the oxa‐Diels‐Alder reaction is achieved by using either a bifunctional amino‐thiourea or a monofunctional quinine organocatalyst under ball‐milling conditions. Liquid‐assisted grinding proves a highly efficient means of affording pyrans in high yield, with high enantiomeric purities and short reaction times.
A LAG to stand on: Liquid‐assisted grinding (LAG) allows enantioselective and diastereodivergent construction of chiral pyran derivatives. The formal oxa‐Diels‐Alder reaction can be directed towards diastereomers by using either mono‐ or bifunctional organocatalysts.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>35146952</pmid><doi>10.1002/cssc.202200028</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-7017-5824</orcidid><orcidid>https://orcid.org/0000-0002-6437-3223</orcidid><orcidid>https://orcid.org/0000-0002-2249-7623</orcidid><orcidid>https://orcid.org/0000-0003-1378-2972</orcidid><orcidid>https://orcid.org/0000-0002-7975-3608</orcidid><orcidid>https://orcid.org/0000-0001-6033-6073</orcidid></addata></record> |
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| subjects | asymmetric synthesis Catalysis Comminution Cycloaddition Reaction Diels-Alder reaction Enantiomers Grinding mills Ketones mechanochemistry O heterocycles organocatalysis Pyrans Stereoisomerism Stereoselectivity Synthesis |
| title | Organocatalytic Diastereodivergent Enantioselective Formal oxa‐Diels‐Alder Reaction of Unsaturated Ketones with Enoates Under Liquid‐Assisted Grinding Conditions |
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