Synthesis of new enantiomerically pure spirooxindolopyrrolizidines via a three-component asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides derived from isatin
An efficient, one-pot, three-component procedure for the synthesis of a small library of new chiral spirooxindolopyrrolizidines with high regio-, diastereo-, and enantioselectivity, from the 1,3-dipolar cycloaddition of azomethine ylides and optically active cinnamoyl oxazolidinone is described. The...
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| Veröffentlicht in: | Tetrahedron letters 2012-09, Vol.53 (38), p.5148-5150 |
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| creator | Taghizadeh, Mohammad Javad Arvinnezhad, Hamid Samadi, Saadi Jadidi, Khosrow Javidan, Abdollah Notash, Behrouz |
| description | An efficient, one-pot, three-component procedure for the synthesis of a small library of new chiral spirooxindolopyrrolizidines with high regio-, diastereo-, and enantioselectivity, from the 1,3-dipolar cycloaddition of azomethine ylides and optically active cinnamoyl oxazolidinone is described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the absence of any Lewis acids. The oxazolidinone chiral auxiliary is removed in a non-destructive manner. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts, and on theoretical calculations. |
| doi_str_mv | 10.1016/j.tetlet.2012.07.066 |
| format | Article |
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The process occurs at room temperature in aqueous ethanol as a green solvent and in the absence of any Lewis acids. The oxazolidinone chiral auxiliary is removed in a non-destructive manner. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts, and on theoretical calculations.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2012.07.066</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Asymmetric 1,3-dipolar ; Asymmetry ; Azomethine ylide ; Chiral auxiliaries ; Chiral spirooxindolopyrrolizidines ; Cycloaddition ; Ethyl alcohol ; Lewis acid ; Mathematical analysis ; Optical activity ; Solvents ; Synthesis (chemistry) ; Three-component reaction</subject><ispartof>Tetrahedron letters, 2012-09, Vol.53 (38), p.5148-5150</ispartof><rights>2012 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c339t-28083b012c7d4474b9276d528256ac87cfb818980d7fcff53af81b59bcfa7b363</citedby><cites>FETCH-LOGICAL-c339t-28083b012c7d4474b9276d528256ac87cfb818980d7fcff53af81b59bcfa7b363</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040403912012415$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Taghizadeh, Mohammad Javad</creatorcontrib><creatorcontrib>Arvinnezhad, Hamid</creatorcontrib><creatorcontrib>Samadi, Saadi</creatorcontrib><creatorcontrib>Jadidi, Khosrow</creatorcontrib><creatorcontrib>Javidan, Abdollah</creatorcontrib><creatorcontrib>Notash, Behrouz</creatorcontrib><title>Synthesis of new enantiomerically pure spirooxindolopyrrolizidines via a three-component asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides derived from isatin</title><title>Tetrahedron letters</title><description>An efficient, one-pot, three-component procedure for the synthesis of a small library of new chiral spirooxindolopyrrolizidines with high regio-, diastereo-, and enantioselectivity, from the 1,3-dipolar cycloaddition of azomethine ylides and optically active cinnamoyl oxazolidinone is described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the absence of any Lewis acids. The oxazolidinone chiral auxiliary is removed in a non-destructive manner. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts, and on theoretical calculations.</description><subject>Asymmetric 1,3-dipolar</subject><subject>Asymmetry</subject><subject>Azomethine ylide</subject><subject>Chiral auxiliaries</subject><subject>Chiral spirooxindolopyrrolizidines</subject><subject>Cycloaddition</subject><subject>Ethyl alcohol</subject><subject>Lewis acid</subject><subject>Mathematical analysis</subject><subject>Optical activity</subject><subject>Solvents</subject><subject>Synthesis (chemistry)</subject><subject>Three-component reaction</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9kc-O1DAMxiMEEsPAG3DIkQPtJk3bZC5IaMU_aSUOwDlKE1fjUZqUJDPQfSlekSzDeX2xD_bvs_0R8pqzljM-3pzaAsVDaTvGu5bJlo3jE7LjSopGDIo_JTvGetb0TByekxc5n1iNUbEd-fNtC-UIGTONMw3wi0IwoWBcIKE13m90PSegecUU428MLvq4bilFj_foMECmFzTU0HJMAI2NyxoDhEJN3pYFSqVQ_lY0DtfoTaJ2sz4a57BqBJrA2H9FFTf3VbQcK5JuHl0Fu7rDBRydU1woZlMwvCTPZuMzvPqf9-THxw_fbz83d18_fbl9f9dYIQ6l6RRTYqrfsNL1veynQydHN3SqG0ZjlbTzpLg6KObkbOd5EGZWfBoOk52NnMQo9uTNlbum-PMMuegFswXvTYB4zprLvh9VJ6vMnvTXVptizglmvSZcTNo0Z_rBH33SV3_0gz-aSV39qWPvrmNQz7ggJJ0tQrDgMIEt2kV8HPAX7mahfA</recordid><startdate>20120919</startdate><enddate>20120919</enddate><creator>Taghizadeh, Mohammad Javad</creator><creator>Arvinnezhad, Hamid</creator><creator>Samadi, Saadi</creator><creator>Jadidi, Khosrow</creator><creator>Javidan, Abdollah</creator><creator>Notash, Behrouz</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20120919</creationdate><title>Synthesis of new enantiomerically pure spirooxindolopyrrolizidines via a three-component asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides derived from isatin</title><author>Taghizadeh, Mohammad Javad ; Arvinnezhad, Hamid ; Samadi, Saadi ; Jadidi, Khosrow ; Javidan, Abdollah ; Notash, Behrouz</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c339t-28083b012c7d4474b9276d528256ac87cfb818980d7fcff53af81b59bcfa7b363</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Asymmetric 1,3-dipolar</topic><topic>Asymmetry</topic><topic>Azomethine ylide</topic><topic>Chiral auxiliaries</topic><topic>Chiral spirooxindolopyrrolizidines</topic><topic>Cycloaddition</topic><topic>Ethyl alcohol</topic><topic>Lewis acid</topic><topic>Mathematical analysis</topic><topic>Optical activity</topic><topic>Solvents</topic><topic>Synthesis (chemistry)</topic><topic>Three-component reaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Taghizadeh, Mohammad Javad</creatorcontrib><creatorcontrib>Arvinnezhad, Hamid</creatorcontrib><creatorcontrib>Samadi, Saadi</creatorcontrib><creatorcontrib>Jadidi, Khosrow</creatorcontrib><creatorcontrib>Javidan, Abdollah</creatorcontrib><creatorcontrib>Notash, Behrouz</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Taghizadeh, Mohammad Javad</au><au>Arvinnezhad, Hamid</au><au>Samadi, Saadi</au><au>Jadidi, Khosrow</au><au>Javidan, Abdollah</au><au>Notash, Behrouz</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of new enantiomerically pure spirooxindolopyrrolizidines via a three-component asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides derived from isatin</atitle><jtitle>Tetrahedron letters</jtitle><date>2012-09-19</date><risdate>2012</risdate><volume>53</volume><issue>38</issue><spage>5148</spage><epage>5150</epage><pages>5148-5150</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>An efficient, one-pot, three-component procedure for the synthesis of a small library of new chiral spirooxindolopyrrolizidines with high regio-, diastereo-, and enantioselectivity, from the 1,3-dipolar cycloaddition of azomethine ylides and optically active cinnamoyl oxazolidinone is described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the absence of any Lewis acids. The oxazolidinone chiral auxiliary is removed in a non-destructive manner. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts, and on theoretical calculations.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2012.07.066</doi><tpages>3</tpages></addata></record> |
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| ispartof | Tetrahedron letters, 2012-09, Vol.53 (38), p.5148-5150 |
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| source | Elsevier ScienceDirect Journals Complete |
| subjects | Asymmetric 1,3-dipolar Asymmetry Azomethine ylide Chiral auxiliaries Chiral spirooxindolopyrrolizidines Cycloaddition Ethyl alcohol Lewis acid Mathematical analysis Optical activity Solvents Synthesis (chemistry) Three-component reaction |
| title | Synthesis of new enantiomerically pure spirooxindolopyrrolizidines via a three-component asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides derived from isatin |
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