Squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones
A highly efficient cinchona alkaloid-derived squaramide catalysed asymmetric Michael/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones was successfully developed. This protocol provides an efficient and mild access to indanone-derived spiropyrr...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2021-09, Vol.19 (33), p.7181-7185 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Hou, Xi-Qiang Wen, Jiang-Bo Yan, Li Du, Da-Ming |
| description | A highly efficient cinchona alkaloid-derived squaramide catalysed asymmetric Michael/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones was successfully developed. This protocol provides an efficient and mild access to indanone-derived spiropyrrolidone scaffolds containing three contiguous stereocenters with two spiroquaternary stereocenters in excellent yields (up to 99%) with high enantio- and diastereoselectivities (up to 99% ee and up to >20 : 1 dr). This method provides an economical and practical approach for the asymmetric synthesis of medicinally relevant molecules.
An efficient squaramide-catalysed asymmetric Michael/cyclization cascade reaction of 4-arylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones afforded indanone-derived spiropyrrolidones in excellent yields with high stereoselectivities. |
| doi_str_mv | 10.1039/d1ob01223a |
| format | Article |
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An efficient squaramide-catalysed asymmetric Michael/cyclization cascade reaction of 4-arylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones afforded indanone-derived spiropyrrolidones in excellent yields with high stereoselectivities.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d1ob01223a</identifier><identifier>PMID: 34378622</identifier><language>eng</language><publisher>CAMBRIDGE: Royal Soc Chemistry</publisher><subject>Asymmetric synthesis ; Asymmetry ; Cascade chemical reactions ; Chemical synthesis ; Chemistry ; Chemistry, Organic ; Crystallography ; Direct reduction ; High-performance liquid chromatography ; Liquid chromatography ; NMR ; Nuclear magnetic resonance ; Physical Sciences ; Science & Technology</subject><ispartof>Organic & biomolecular chemistry, 2021-09, Vol.19 (33), p.7181-7185</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>10</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000683433400001</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c337t-8a59a52c0ac32f3b51356fd2ac271676d6044c5905b858efa67f184058aee0433</citedby><cites>FETCH-LOGICAL-c337t-8a59a52c0ac32f3b51356fd2ac271676d6044c5905b858efa67f184058aee0433</cites><orcidid>0000-0002-9924-5117</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,782,786,27931,27932,39265</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34378622$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hou, Xi-Qiang</creatorcontrib><creatorcontrib>Wen, Jiang-Bo</creatorcontrib><creatorcontrib>Yan, Li</creatorcontrib><creatorcontrib>Du, Da-Ming</creatorcontrib><title>Squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones</title><title>Organic & biomolecular chemistry</title><addtitle>ORG BIOMOL CHEM</addtitle><addtitle>Org Biomol Chem</addtitle><description>A highly efficient cinchona alkaloid-derived squaramide catalysed asymmetric Michael/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones was successfully developed. This protocol provides an efficient and mild access to indanone-derived spiropyrrolidone scaffolds containing three contiguous stereocenters with two spiroquaternary stereocenters in excellent yields (up to 99%) with high enantio- and diastereoselectivities (up to 99% ee and up to >20 : 1 dr). This method provides an economical and practical approach for the asymmetric synthesis of medicinally relevant molecules.
An efficient squaramide-catalysed asymmetric Michael/cyclization cascade reaction of 4-arylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones afforded indanone-derived spiropyrrolidones in excellent yields with high stereoselectivities.</description><subject>Asymmetric synthesis</subject><subject>Asymmetry</subject><subject>Cascade chemical reactions</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry, Organic</subject><subject>Crystallography</subject><subject>Direct reduction</subject><subject>High-performance liquid chromatography</subject><subject>Liquid chromatography</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Physical Sciences</subject><subject>Science & Technology</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>HGBXW</sourceid><recordid>eNqN0k1v1DAQBuAIgWgpXLiDIvWCAFN_xsmxLJ9SUQ_AOZrYE62rxN7aiUr6U_pr8e6WReLEyaPRMyPLr4viOaPvGBXNmWWho4xzAQ-KYya1JlSJ5uGh5vSoeJLSFaWs0ZV8XBwJKXRdcX5c3H2_niHC6CwSAxMMS0JbQlrGEafoTPnNmTXgUIK1bnLBn5nFDO4WtnVpIBmwWEYEs2uEvpQE4jLk6fUy5K0eCX8riHXhV9gsMYbcdB5TeeOmdcmJS2Fau2AW8DAFwojzFnzI4mnxqIch4bP786T4-enjj9UXcnH5-evq_IIYIfREalANKG4oGMF70SkmVNVbDoZrVunKVlRKoxqqulrV2EOle1ZLqmpApFKIk-LVfu8mhusZ09SOLhkcBvAY5tRyVVHeaC1Vpqf_0KswR59vt1WSCi15k9XrvTIxpBSxbzfRjflVWkbbbWLtB3b5fpfYecYv71fO3Yj2QP9ElEG9BzfYhT4Zh97ggVFKqzpbIXNF2cpNu2RWYfZTHn3z_6NZv9jrmMwB_f1b4jcul718</recordid><startdate>20210907</startdate><enddate>20210907</enddate><creator>Hou, Xi-Qiang</creator><creator>Wen, Jiang-Bo</creator><creator>Yan, Li</creator><creator>Du, Da-Ming</creator><general>Royal Soc Chemistry</general><general>Royal Society of Chemistry</general><scope>1KM</scope><scope>1KN</scope><scope>BLEPL</scope><scope>DTL</scope><scope>HGBXW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-9924-5117</orcidid></search><sort><creationdate>20210907</creationdate><title>Squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones</title><author>Hou, Xi-Qiang ; Wen, Jiang-Bo ; Yan, Li ; Du, Da-Ming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-8a59a52c0ac32f3b51356fd2ac271676d6044c5905b858efa67f184058aee0433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Asymmetric synthesis</topic><topic>Asymmetry</topic><topic>Cascade chemical reactions</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry, Organic</topic><topic>Crystallography</topic><topic>Direct reduction</topic><topic>High-performance liquid chromatography</topic><topic>Liquid chromatography</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Physical Sciences</topic><topic>Science & Technology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hou, Xi-Qiang</creatorcontrib><creatorcontrib>Wen, Jiang-Bo</creatorcontrib><creatorcontrib>Yan, Li</creatorcontrib><creatorcontrib>Du, Da-Ming</creatorcontrib><collection>Index Chemicus</collection><collection>Current Chemical Reactions</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>Web of Science - Science Citation Index Expanded - 2021</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hou, Xi-Qiang</au><au>Wen, Jiang-Bo</au><au>Yan, Li</au><au>Du, Da-Ming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones</atitle><jtitle>Organic & biomolecular chemistry</jtitle><stitle>ORG BIOMOL CHEM</stitle><addtitle>Org Biomol Chem</addtitle><date>2021-09-07</date><risdate>2021</risdate><volume>19</volume><issue>33</issue><spage>7181</spage><epage>7185</epage><pages>7181-7185</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A highly efficient cinchona alkaloid-derived squaramide catalysed asymmetric Michael/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones was successfully developed. This protocol provides an efficient and mild access to indanone-derived spiropyrrolidone scaffolds containing three contiguous stereocenters with two spiroquaternary stereocenters in excellent yields (up to 99%) with high enantio- and diastereoselectivities (up to 99% ee and up to >20 : 1 dr). This method provides an economical and practical approach for the asymmetric synthesis of medicinally relevant molecules.
An efficient squaramide-catalysed asymmetric Michael/cyclization cascade reaction of 4-arylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones afforded indanone-derived spiropyrrolidones in excellent yields with high stereoselectivities.</abstract><cop>CAMBRIDGE</cop><pub>Royal Soc Chemistry</pub><pmid>34378622</pmid><doi>10.1039/d1ob01223a</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-9924-5117</orcidid></addata></record> |
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| subjects | Asymmetric synthesis Asymmetry Cascade chemical reactions Chemical synthesis Chemistry Chemistry, Organic Crystallography Direct reduction High-performance liquid chromatography Liquid chromatography NMR Nuclear magnetic resonance Physical Sciences Science & Technology |
| title | Squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones |
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