A General Route to Mono- and Disubstituted Divinyl Sulfones: Acyclic Michael Acceptors for the Synthesis of Polyfunctionalized Cyclic Sulfones
Nucleophilic C−S bond formation using easily available β-hydroxysulfonate derivatives allowed direct access to new mono- and disubstituted divinyl sulfones. Our strategy uses thioethanol (HSCH2CH2OH) and its analogues such as HSCH2CH(Y)OH generated in situ. The strategy also allows the synthesis of...
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| Veröffentlicht in: | Journal of organic chemistry 2011-05, Vol.76 (9), p.3034-3041 |
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| container_end_page | 3041 |
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| container_title | Journal of organic chemistry |
| container_volume | 76 |
| creator | Pal, Tarun Kumar Dey, Santu Pathak, Tanmaya |
| description | Nucleophilic C−S bond formation using easily available β-hydroxysulfonate derivatives allowed direct access to new mono- and disubstituted divinyl sulfones. Our strategy uses thioethanol (HSCH2CH2OH) and its analogues such as HSCH2CH(Y)OH generated in situ. The strategy also allows the synthesis of modified divinyl sulfones attached to chiral appendages like carbohydrates. Bis-heteronucleophilic Michael addition reactions with 1 equiv of a primary amine afforded new generations of S,S-dioxothiomorpholine derivatives known for their therapeutic applications. Further synthetic manipulations of some of these cyclic compounds led to the synthesis of novel bicyclic derivatives. |
| doi_str_mv | 10.1021/jo101877r |
| format | Article |
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Org. Chem</addtitle><description>Nucleophilic C−S bond formation using easily available β-hydroxysulfonate derivatives allowed direct access to new mono- and disubstituted divinyl sulfones. Our strategy uses thioethanol (HSCH2CH2OH) and its analogues such as HSCH2CH(Y)OH generated in situ. The strategy also allows the synthesis of modified divinyl sulfones attached to chiral appendages like carbohydrates. Bis-heteronucleophilic Michael addition reactions with 1 equiv of a primary amine afforded new generations of S,S-dioxothiomorpholine derivatives known for their therapeutic applications. Further synthetic manipulations of some of these cyclic compounds led to the synthesis of novel bicyclic derivatives.</description><subject>Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis</subject><subject>Bridged Bicyclo Compounds, Heterocyclic - chemistry</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Sulfones - chemical synthesis</subject><subject>Sulfones - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMFO3DAQhq2qqGxpD32BypcKcUhrO07scFstlCKBWgE9R45jCyOvvXgcpPAQfeYa7QIX5jCj0Xz6RvoR-kLJd0oY_XEXKaFSiPQOLWjDSNV2hL9HC0IYq2rW1vvoI8AdKdU0zQe0zyivZdPJBfq3xGcmmKQ8vopTNjhHfBlDrLAKIz5xMA2QXS6Xp-3Bhdnj68nbGAwc46WetXcaXzp9q4wvuzabHBNgGxPOtwZfz6EMcICjxX-in-0UdHYxKO8ei3O1FTwrP6E9qzyYz7t5gP7-PL1Z_aoufp-dr5YXlao5z1VjjZB07AQRDRm4FiNTmmlBLa-tIINodSMFk0Mnu04TQ1s6Ks7t2ApJzKDrA3S49W5SvJ8M5H7tQBvvVTBxgl62nHacEVLIoy2pUwRIxvab5NYqzT0l_VP6_Uv6hf26s07D2owv5HPcBfi2AxRo5W1SQTt45TilsrRXTmko_imVuOCNh_8Bg4GaEQ</recordid><startdate>20110506</startdate><enddate>20110506</enddate><creator>Pal, Tarun Kumar</creator><creator>Dey, Santu</creator><creator>Pathak, Tanmaya</creator><general>American Chemical Society</general><scope>IQODW</scope><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>20110506</creationdate><title>A General Route to Mono- and Disubstituted Divinyl Sulfones: Acyclic Michael Acceptors for the Synthesis of Polyfunctionalized Cyclic Sulfones</title><author>Pal, Tarun Kumar ; Dey, Santu ; Pathak, Tanmaya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-5fe781d970750b4c7d2ac2c71f43f70b76c58728b9899c0e161da44fd6780ebc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis</topic><topic>Bridged Bicyclo Compounds, Heterocyclic - chemistry</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><topic>Sulfones - chemical synthesis</topic><topic>Sulfones - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pal, Tarun Kumar</creatorcontrib><creatorcontrib>Dey, Santu</creatorcontrib><creatorcontrib>Pathak, Tanmaya</creatorcontrib><collection>Pascal-Francis</collection><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>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pal, Tarun Kumar</au><au>Dey, Santu</au><au>Pathak, Tanmaya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A General Route to Mono- and Disubstituted Divinyl Sulfones: Acyclic Michael Acceptors for the Synthesis of Polyfunctionalized Cyclic Sulfones</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2011-05-06</date><risdate>2011</risdate><volume>76</volume><issue>9</issue><spage>3034</spage><epage>3041</epage><pages>3034-3041</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Nucleophilic C−S bond formation using easily available β-hydroxysulfonate derivatives allowed direct access to new mono- and disubstituted divinyl sulfones. Our strategy uses thioethanol (HSCH2CH2OH) and its analogues such as HSCH2CH(Y)OH generated in situ. The strategy also allows the synthesis of modified divinyl sulfones attached to chiral appendages like carbohydrates. Bis-heteronucleophilic Michael addition reactions with 1 equiv of a primary amine afforded new generations of S,S-dioxothiomorpholine derivatives known for their therapeutic applications. 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| ispartof | Journal of organic chemistry, 2011-05, Vol.76 (9), p.3034-3041 |
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| language | eng |
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| subjects | Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis Bridged Bicyclo Compounds, Heterocyclic - chemistry Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Organic chemistry Preparations and properties Stereoisomerism Sulfones - chemical synthesis Sulfones - chemistry |
| title | A General Route to Mono- and Disubstituted Divinyl Sulfones: Acyclic Michael Acceptors for the Synthesis of Polyfunctionalized Cyclic Sulfones |
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