A general method for the facile synthesis of optically active 2-substituted piperazines via functionalized 2,5-diketopiperazines
[Display omitted] Upon utilization of some common methods described in the literature for the synthesis of chiral, 2-substituted 2,5-diketopiperazines, extensive racemization was observed. Further investigation showed that heating in the presence of a mild base racemized the chiral center in the pro...
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| Veröffentlicht in: | Tetrahedron letters 2014-08, Vol.55 (32), p.4501-4504 |
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| container_title | Tetrahedron letters |
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| creator | Ashton, Kate S. Denti, Mitchell Norman, Mark H. St. Jean, David J. |
| description | [Display omitted]
Upon utilization of some common methods described in the literature for the synthesis of chiral, 2-substituted 2,5-diketopiperazines, extensive racemization was observed. Further investigation showed that heating in the presence of a mild base racemized the chiral center in the product diketopiperazines. A generalized, readily scalable route was sought and, after investigating the effect of base and temperature, conditions were identified that promoted cyclization without erosion of enantiomeric excess. An array of functionalization was tolerated and this procedure serves as a useful and reliable method for the facile synthesis of this important class of compounds. |
| doi_str_mv | 10.1016/j.tetlet.2014.06.058 |
| format | Article |
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Upon utilization of some common methods described in the literature for the synthesis of chiral, 2-substituted 2,5-diketopiperazines, extensive racemization was observed. Further investigation showed that heating in the presence of a mild base racemized the chiral center in the product diketopiperazines. A generalized, readily scalable route was sought and, after investigating the effect of base and temperature, conditions were identified that promoted cyclization without erosion of enantiomeric excess. An array of functionalization was tolerated and this procedure serves as a useful and reliable method for the facile synthesis of this important class of compounds.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2014.06.058</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>2-Substituted 2,5-diketopiperazine ; 2-Substituted piperazine ; Amino acid cyclization ; Arrays ; Erosion ; Fischer method ; Heating ; Optical activity ; Racemization ; Synthesis (chemistry) ; Tetrahedrons ; Utilization</subject><ispartof>Tetrahedron letters, 2014-08, Vol.55 (32), p.4501-4504</ispartof><rights>2014 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c405t-3a59b211d6e2b1859bc59e3846957c24ee748077c75dca79648070d2b34c66953</citedby><cites>FETCH-LOGICAL-c405t-3a59b211d6e2b1859bc59e3846957c24ee748077c75dca79648070d2b34c66953</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040403914010491$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Ashton, Kate S.</creatorcontrib><creatorcontrib>Denti, Mitchell</creatorcontrib><creatorcontrib>Norman, Mark H.</creatorcontrib><creatorcontrib>St. Jean, David J.</creatorcontrib><title>A general method for the facile synthesis of optically active 2-substituted piperazines via functionalized 2,5-diketopiperazines</title><title>Tetrahedron letters</title><description>[Display omitted]
Upon utilization of some common methods described in the literature for the synthesis of chiral, 2-substituted 2,5-diketopiperazines, extensive racemization was observed. Further investigation showed that heating in the presence of a mild base racemized the chiral center in the product diketopiperazines. A generalized, readily scalable route was sought and, after investigating the effect of base and temperature, conditions were identified that promoted cyclization without erosion of enantiomeric excess. An array of functionalization was tolerated and this procedure serves as a useful and reliable method for the facile synthesis of this important class of compounds.</description><subject>2-Substituted 2,5-diketopiperazine</subject><subject>2-Substituted piperazine</subject><subject>Amino acid cyclization</subject><subject>Arrays</subject><subject>Erosion</subject><subject>Fischer method</subject><subject>Heating</subject><subject>Optical activity</subject><subject>Racemization</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><subject>Utilization</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kL1PwzAQxS0EEuXjP2DwyEDCOXHiZEGqEF9SJRaYLde5gIsbB9upVCb-dFyVgYlbTk_3e0-6R8gFg5wBq69XecRoMeYFMJ5DnUPVHJAZa0SZlVXDDskMgEPGoWyPyUkIK0hTNzAj33P6hgN6Zeka47vraO88je9Ie6WNRRq2Q1LBBOp66sZotLJ2S5WOZoO0yMK0DNHEKWJHRzOmpC8zYKAbo2g_DQlzg7LmK52LqyrrzAdG9wc8I0e9sgHPf_cpeb2_e7l9zBbPD0-380WmOVQxK1XVLgvGuhqLJWuS0FWLZcPrthK64IiCNyCEFlWnlWjrnYKuWJZc14kpT8nlPnf07nPCEOXaBI3WqgHdFCQTPGWxUkBC-R7V3oXgsZejN2vlt5KB3BUuV3JfuNwVLqGWqfBku9nbML2xMehl0AYHjZ3xqKPsnPk_4AcyII1K</recordid><startdate>20140806</startdate><enddate>20140806</enddate><creator>Ashton, Kate S.</creator><creator>Denti, Mitchell</creator><creator>Norman, Mark H.</creator><creator>St. Jean, David J.</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>20140806</creationdate><title>A general method for the facile synthesis of optically active 2-substituted piperazines via functionalized 2,5-diketopiperazines</title><author>Ashton, Kate S. ; Denti, Mitchell ; Norman, Mark H. ; St. Jean, David J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c405t-3a59b211d6e2b1859bc59e3846957c24ee748077c75dca79648070d2b34c66953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>2-Substituted 2,5-diketopiperazine</topic><topic>2-Substituted piperazine</topic><topic>Amino acid cyclization</topic><topic>Arrays</topic><topic>Erosion</topic><topic>Fischer method</topic><topic>Heating</topic><topic>Optical activity</topic><topic>Racemization</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><topic>Utilization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ashton, Kate S.</creatorcontrib><creatorcontrib>Denti, Mitchell</creatorcontrib><creatorcontrib>Norman, Mark H.</creatorcontrib><creatorcontrib>St. Jean, David J.</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>Ashton, Kate S.</au><au>Denti, Mitchell</au><au>Norman, Mark H.</au><au>St. Jean, David J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A general method for the facile synthesis of optically active 2-substituted piperazines via functionalized 2,5-diketopiperazines</atitle><jtitle>Tetrahedron letters</jtitle><date>2014-08-06</date><risdate>2014</risdate><volume>55</volume><issue>32</issue><spage>4501</spage><epage>4504</epage><pages>4501-4504</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
Upon utilization of some common methods described in the literature for the synthesis of chiral, 2-substituted 2,5-diketopiperazines, extensive racemization was observed. Further investigation showed that heating in the presence of a mild base racemized the chiral center in the product diketopiperazines. A generalized, readily scalable route was sought and, after investigating the effect of base and temperature, conditions were identified that promoted cyclization without erosion of enantiomeric excess. An array of functionalization was tolerated and this procedure serves as a useful and reliable method for the facile synthesis of this important class of compounds.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2014.06.058</doi><tpages>4</tpages></addata></record> |
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| ispartof | Tetrahedron letters, 2014-08, Vol.55 (32), p.4501-4504 |
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| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | 2-Substituted 2,5-diketopiperazine 2-Substituted piperazine Amino acid cyclization Arrays Erosion Fischer method Heating Optical activity Racemization Synthesis (chemistry) Tetrahedrons Utilization |
| title | A general method for the facile synthesis of optically active 2-substituted piperazines via functionalized 2,5-diketopiperazines |
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