Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products
Aziridinyl imines are well-known carbene equivalents because they are precursors of diazo compounds from which reactive intermediates can be produced. These carbene equivalents can be utilized as zwitterionic species, diradicals, or 4π system for cycloaddition reactions. Thus, the intermediates deri...
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| Veröffentlicht in: | Pure and applied chemistry 2013-01, Vol.85 (4), p.741-753 |
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| creator | Lee, Hee-Yoon Song, Seog-Beom Kang, Taek Kim, Yoon Jung Geum, Su Jeong |
| description | Aziridinyl imines are well-known carbene equivalents because they are precursors of diazo compounds from which reactive intermediates can be produced. These carbene equivalents can be utilized as zwitterionic species, diradicals, or 4π system for cycloaddition reactions. Thus, the intermediates derived from aziridinyl imines have been used in the sulfur-ylide-mediated epoxide formation, tandem free-radical reactions, or cyclopropanation reaction via carbene intermediates to form trimethylenemethane (TMM) diyls, which undergo [2 + 3] cycloaddition reactions to form cyclopentanoids. Diazo compounds generated from aziridinyl imines also react with allenes to form TMM diyls. This reaction was utilized in tandem cycloaddition reactions of linear substrates to form polyquinanes. These tandem reaction strategies were successfully applied to the total synthesis of various cyclopentanoid natural products. |
| doi_str_mv | 10.1351/PAC-CON-12-10-01 |
| format | Article |
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These carbene equivalents can be utilized as zwitterionic species, diradicals, or 4π system for cycloaddition reactions. Thus, the intermediates derived from aziridinyl imines have been used in the sulfur-ylide-mediated epoxide formation, tandem free-radical reactions, or cyclopropanation reaction via carbene intermediates to form trimethylenemethane (TMM) diyls, which undergo [2 + 3] cycloaddition reactions to form cyclopentanoids. Diazo compounds generated from aziridinyl imines also react with allenes to form TMM diyls. This reaction was utilized in tandem cycloaddition reactions of linear substrates to form polyquinanes. These tandem reaction strategies were successfully applied to the total synthesis of various cyclopentanoid natural products.</description><identifier>ISSN: 0033-4545</identifier><identifier>EISSN: 1365-3075</identifier><identifier>DOI: 10.1351/PAC-CON-12-10-01</identifier><language>eng</language><publisher>Berlin: De Gruyter</publisher><subject>Cascade chemical reactions ; Chemical bonds ; Chemical synthesis ; Cycloaddition ; cycloadditions ; domino reactions ; Equivalence ; hydrazones ; Imines ; Natural products ; polycyclic compounds ; radical reactions ; Substrates ; tandem reactions ; total synthesis ; trimethylenemethane</subject><ispartof>Pure and applied chemistry, 2013-01, Vol.85 (4), p.741-753</ispartof><rights>2013 Walter de Gruyter GmbH, Berlin/Boston</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c405t-852b2280d699f0037e5e4ede74c540fc7d00b52c6abaf2fca4c9a55c4f0e08023</citedby><cites>FETCH-LOGICAL-c405t-852b2280d699f0037e5e4ede74c540fc7d00b52c6abaf2fca4c9a55c4f0e08023</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Lee, Hee-Yoon</creatorcontrib><creatorcontrib>Song, Seog-Beom</creatorcontrib><creatorcontrib>Kang, Taek</creatorcontrib><creatorcontrib>Kim, Yoon Jung</creatorcontrib><creatorcontrib>Geum, Su Jeong</creatorcontrib><title>Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products</title><title>Pure and applied chemistry</title><description>Aziridinyl imines are well-known carbene equivalents because they are precursors of diazo compounds from which reactive intermediates can be produced. 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These tandem reaction strategies were successfully applied to the total synthesis of various cyclopentanoid natural products.</description><subject>Cascade chemical reactions</subject><subject>Chemical bonds</subject><subject>Chemical synthesis</subject><subject>Cycloaddition</subject><subject>cycloadditions</subject><subject>domino reactions</subject><subject>Equivalence</subject><subject>hydrazones</subject><subject>Imines</subject><subject>Natural products</subject><subject>polycyclic compounds</subject><subject>radical reactions</subject><subject>Substrates</subject><subject>tandem reactions</subject><subject>total synthesis</subject><subject>trimethylenemethane</subject><issn>0033-4545</issn><issn>1365-3075</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNp1UEtLAzEQDqJgrd49BjxHJ9mku-tBKPUJoh70vKTZ2Zqyza5JVqm_wJ9tagVPwsAMM9-D-Qg55nDKM8XPnqYzNnt8YFwwDgz4DhnxbKJYBrnaJSOALGNSSbVPDkJYAoAspRiRr-mn9ba2bt1Su7IOA7WOdn6hnTU0rF18xWDDOb3Ed2y7foUu0q6hUbsaV9SjNtF2jobodcSFTfx0obrvW2v0zyl2qaJu_9Q2Ak7Hwadl77t6MDEckr1GtwGPfvuYvFxfPc9u2f3jzd1ses-MBBVZocRciALqSVk26akcFUqsMZdGSWhMXgPMlTATPdeNaIyWptRKGdkAQgEiG5OTrW4yfhswxGrZDd4ly0qIDHhZ8AlPKNiijO9C8NhUvbcr7dcVh2qTd5XyrlLeFRebFWwoF1vKh24j-hoXflin4U__P2qhZC559g1oqYtb</recordid><startdate>20130101</startdate><enddate>20130101</enddate><creator>Lee, Hee-Yoon</creator><creator>Song, Seog-Beom</creator><creator>Kang, Taek</creator><creator>Kim, Yoon Jung</creator><creator>Geum, Su Jeong</creator><general>De Gruyter</general><general>Walter de Gruyter GmbH</general><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FE</scope><scope>8FG</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>M0S</scope><scope>M1P</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope></search><sort><creationdate>20130101</creationdate><title>Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products</title><author>Lee, Hee-Yoon ; 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These carbene equivalents can be utilized as zwitterionic species, diradicals, or 4π system for cycloaddition reactions. Thus, the intermediates derived from aziridinyl imines have been used in the sulfur-ylide-mediated epoxide formation, tandem free-radical reactions, or cyclopropanation reaction via carbene intermediates to form trimethylenemethane (TMM) diyls, which undergo [2 + 3] cycloaddition reactions to form cyclopentanoids. Diazo compounds generated from aziridinyl imines also react with allenes to form TMM diyls. This reaction was utilized in tandem cycloaddition reactions of linear substrates to form polyquinanes. These tandem reaction strategies were successfully applied to the total synthesis of various cyclopentanoid natural products.</abstract><cop>Berlin</cop><pub>De Gruyter</pub><doi>10.1351/PAC-CON-12-10-01</doi><tpages>13</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Cascade chemical reactions Chemical bonds Chemical synthesis Cycloaddition cycloadditions domino reactions Equivalence hydrazones Imines Natural products polycyclic compounds radical reactions Substrates tandem reactions total synthesis trimethylenemethane |
| title | Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products |
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