Enantioselective Alkylation of Amino Acid Derivatives Promoted by Cyclic Peptoids under Phase-Transfer Conditions
The effects of substituents and cavity size on catalytic efficiency of proline-rich cyclopeptoids under phase-transfer conditions were studied. High affinity constants (K a) for the sodium and potassium cations, comparable to those reported for crown ethers, were observed for an alternated N-benzylg...
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| Veröffentlicht in: | Journal of organic chemistry 2016-03, Vol.81 (6), p.2494-2505 |
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| container_title | Journal of organic chemistry |
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| creator | Schettini, Rosaria De Riccardis, Francesco Della Sala, Giorgio Izzo, Irene |
| description | The effects of substituents and cavity size on catalytic efficiency of proline-rich cyclopeptoids under phase-transfer conditions were studied. High affinity constants (K a) for the sodium and potassium cations, comparable to those reported for crown ethers, were observed for an alternated N-benzylglycine/l-proline hexameric cyclopeptoid. This compound was found to catalyze the alkylation of N-(diphenylmethylene)glycine cumyl ester in values of enantioselectivities comparable with those reported for the Cinchona alkaloid ammonium salts derivatives (83–96% ee), and with lower catalyst loading (1–2.5% mol), in the presence of a broad range of benzyl, allyl and alkyl halides. |
| doi_str_mv | 10.1021/acs.joc.6b00065 |
| format | Article |
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High affinity constants (K a) for the sodium and potassium cations, comparable to those reported for crown ethers, were observed for an alternated N-benzylglycine/l-proline hexameric cyclopeptoid. This compound was found to catalyze the alkylation of N-(diphenylmethylene)glycine cumyl ester in values of enantioselectivities comparable with those reported for the Cinchona alkaloid ammonium salts derivatives (83–96% ee), and with lower catalyst loading (1–2.5% mol), in the presence of a broad range of benzyl, allyl and alkyl halides.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.6b00065</identifier><identifier>PMID: 26914694</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkylation ; Arginine - chemistry ; Benzene Derivatives - chemistry ; Cinchona Alkaloids - chemistry ; Glycine - analogs & derivatives ; Glycine - chemistry ; Molecular Structure ; Peptides, Cyclic - chemistry ; Proline - analogs & derivatives ; Proline - chemistry ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2016-03, Vol.81 (6), p.2494-2505</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-ca4c32739b6420ff23d3088ec1f75f5b026a8e5c5968ed75a21bbbeba6e1d3433</citedby><cites>FETCH-LOGICAL-a333t-ca4c32739b6420ff23d3088ec1f75f5b026a8e5c5968ed75a21bbbeba6e1d3433</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.6b00065$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.6b00065$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26914694$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Schettini, Rosaria</creatorcontrib><creatorcontrib>De Riccardis, Francesco</creatorcontrib><creatorcontrib>Della Sala, Giorgio</creatorcontrib><creatorcontrib>Izzo, Irene</creatorcontrib><title>Enantioselective Alkylation of Amino Acid Derivatives Promoted by Cyclic Peptoids under Phase-Transfer Conditions</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The effects of substituents and cavity size on catalytic efficiency of proline-rich cyclopeptoids under phase-transfer conditions were studied. High affinity constants (K a) for the sodium and potassium cations, comparable to those reported for crown ethers, were observed for an alternated N-benzylglycine/l-proline hexameric cyclopeptoid. This compound was found to catalyze the alkylation of N-(diphenylmethylene)glycine cumyl ester in values of enantioselectivities comparable with those reported for the Cinchona alkaloid ammonium salts derivatives (83–96% ee), and with lower catalyst loading (1–2.5% mol), in the presence of a broad range of benzyl, allyl and alkyl halides.</description><subject>Alkylation</subject><subject>Arginine - chemistry</subject><subject>Benzene Derivatives - chemistry</subject><subject>Cinchona Alkaloids - chemistry</subject><subject>Glycine - analogs & derivatives</subject><subject>Glycine - chemistry</subject><subject>Molecular Structure</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Proline - analogs & derivatives</subject><subject>Proline - chemistry</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kE1P4zAQhi0Egm7hzA35iITS-iN2kmPVBXYlpO0BzpE_JsKQ2MVOkPrv11ULN06jGT3vK82D0DUlC0oYXSqTFm_BLKQmhEhxgmZUMFLIhpSnaEYIYwVnkl-gXym9ZYQIIc7RBZMNLWVTztDHvVd-dCFBD2Z0n4BX_fuuV_nkcejwanA-4JVxFv-G6D7Vnkl4E8MQRrBY7_B6Z3pn8Aa2Y3A24clbiHjzqhIUz1H51OV1Hbx1-9J0ic461Se4Os45enm4f17_KZ7-Pf5dr54KxTkfC6NKw1nFGy1LRrqOcctJXYOhXSU6oQmTqgZhRCNrsJVQjGqtQSsJ1PKS8zm6PfRuY_iYII3t4JKBvlcewpRaWlWlYE3dlBldHlATQ0oRunYb3aDirqWk3Xtus-c2e26PnnPi5lg-6QHsN_8lNgN3B-CQnKLPv_5Y9x8hsYpc</recordid><startdate>20160318</startdate><enddate>20160318</enddate><creator>Schettini, Rosaria</creator><creator>De Riccardis, Francesco</creator><creator>Della Sala, Giorgio</creator><creator>Izzo, Irene</creator><general>American Chemical Society</general><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>20160318</creationdate><title>Enantioselective Alkylation of Amino Acid Derivatives Promoted by Cyclic Peptoids under Phase-Transfer Conditions</title><author>Schettini, Rosaria ; De Riccardis, Francesco ; Della Sala, Giorgio ; Izzo, Irene</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-ca4c32739b6420ff23d3088ec1f75f5b026a8e5c5968ed75a21bbbeba6e1d3433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Alkylation</topic><topic>Arginine - chemistry</topic><topic>Benzene Derivatives - chemistry</topic><topic>Cinchona Alkaloids - chemistry</topic><topic>Glycine - analogs & derivatives</topic><topic>Glycine - chemistry</topic><topic>Molecular Structure</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Proline - analogs & derivatives</topic><topic>Proline - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Schettini, Rosaria</creatorcontrib><creatorcontrib>De Riccardis, Francesco</creatorcontrib><creatorcontrib>Della Sala, Giorgio</creatorcontrib><creatorcontrib>Izzo, Irene</creatorcontrib><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>Schettini, Rosaria</au><au>De Riccardis, Francesco</au><au>Della Sala, Giorgio</au><au>Izzo, Irene</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Alkylation of Amino Acid Derivatives Promoted by Cyclic Peptoids under Phase-Transfer Conditions</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2016-03-18</date><risdate>2016</risdate><volume>81</volume><issue>6</issue><spage>2494</spage><epage>2505</epage><pages>2494-2505</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The effects of substituents and cavity size on catalytic efficiency of proline-rich cyclopeptoids under phase-transfer conditions were studied. High affinity constants (K a) for the sodium and potassium cations, comparable to those reported for crown ethers, were observed for an alternated N-benzylglycine/l-proline hexameric cyclopeptoid. This compound was found to catalyze the alkylation of N-(diphenylmethylene)glycine cumyl ester in values of enantioselectivities comparable with those reported for the Cinchona alkaloid ammonium salts derivatives (83–96% ee), and with lower catalyst loading (1–2.5% mol), in the presence of a broad range of benzyl, allyl and alkyl halides.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26914694</pmid><doi>10.1021/acs.joc.6b00065</doi><tpages>12</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2016-03, Vol.81 (6), p.2494-2505 |
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| source | ACS Publications; MEDLINE |
| subjects | Alkylation Arginine - chemistry Benzene Derivatives - chemistry Cinchona Alkaloids - chemistry Glycine - analogs & derivatives Glycine - chemistry Molecular Structure Peptides, Cyclic - chemistry Proline - analogs & derivatives Proline - chemistry Stereoisomerism |
| title | Enantioselective Alkylation of Amino Acid Derivatives Promoted by Cyclic Peptoids under Phase-Transfer Conditions |
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