Enantioselective Synthesis of Near Enantiopure Compound by Asymmetric Autocatalysis Triggered by Asymmetric Photolysis with Circularly Polarized Light
Right- and left-handed circularly polarized light (CPL) has been proposed as one of the origins of homochirality of biomolecules. However, the enantiomeric excess induced by CPL has been only very low (99.5% ee. On the other hand, irradiation with l-CPL affords (S)-pyrimidyl alkanol with >99.5% e...
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| Veröffentlicht in: | Journal of the American Chemical Society 2005-03, Vol.127 (10), p.3274-3275 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 127 |
| creator | Kawasaki, Tsuneomi Sato, Mirai Ishiguro, Saori Saito, Takahiro Morishita, Yosuke Sato, Itaru Nishino, Hideo Inoue, Yoshihisa Soai, Kenso |
| description | Right- and left-handed circularly polarized light (CPL) has been proposed as one of the origins of homochirality of biomolecules. However, the enantiomeric excess induced by CPL has been only very low (99.5% ee. On the other hand, irradiation with l-CPL affords (S)-pyrimidyl alkanol with >99.5% ee. Thus, chiral physical power, such as CPL, in conjunction with asymmetric autocatalysis, provides a highly enantioenriched compound. |
| doi_str_mv | 10.1021/ja0422108 |
| format | Article |
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However, the enantiomeric excess induced by CPL has been only very low (<2% ee). We found the unprecedented example of asymmetric autocatalysis triggered directly by a chiral physical factor, that is, right- and left-handed CPL, leading to a near enantiopure compound. Asymmetric photolysis of racemic pyrimidyl alkanol by r-CPL irradiation followed by asymmetric autocatalysis affords (R)-pyrimidyl alkanol with >99.5% ee. On the other hand, irradiation with l-CPL affords (S)-pyrimidyl alkanol with >99.5% ee. Thus, chiral physical power, such as CPL, in conjunction with asymmetric autocatalysis, provides a highly enantioenriched compound.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja0422108</identifier><identifier>PMID: 15755133</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of the American Chemical Society, 2005-03, Vol.127 (10), p.3274-3275</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-ee7e4a734024f330714072fb491251282a163d641959331b3f31a385b862cda63</citedby><cites>FETCH-LOGICAL-a381t-ee7e4a734024f330714072fb491251282a163d641959331b3f31a385b862cda63</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/ja0422108$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja0422108$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2764,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16758612$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15755133$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kawasaki, Tsuneomi</creatorcontrib><creatorcontrib>Sato, Mirai</creatorcontrib><creatorcontrib>Ishiguro, Saori</creatorcontrib><creatorcontrib>Saito, Takahiro</creatorcontrib><creatorcontrib>Morishita, Yosuke</creatorcontrib><creatorcontrib>Sato, Itaru</creatorcontrib><creatorcontrib>Nishino, Hideo</creatorcontrib><creatorcontrib>Inoue, Yoshihisa</creatorcontrib><creatorcontrib>Soai, Kenso</creatorcontrib><title>Enantioselective Synthesis of Near Enantiopure Compound by Asymmetric Autocatalysis Triggered by Asymmetric Photolysis with Circularly Polarized Light</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Right- and left-handed circularly polarized light (CPL) has been proposed as one of the origins of homochirality of biomolecules. However, the enantiomeric excess induced by CPL has been only very low (<2% ee). We found the unprecedented example of asymmetric autocatalysis triggered directly by a chiral physical factor, that is, right- and left-handed CPL, leading to a near enantiopure compound. Asymmetric photolysis of racemic pyrimidyl alkanol by r-CPL irradiation followed by asymmetric autocatalysis affords (R)-pyrimidyl alkanol with >99.5% ee. On the other hand, irradiation with l-CPL affords (S)-pyrimidyl alkanol with >99.5% ee. Thus, chiral physical power, such as CPL, in conjunction with asymmetric autocatalysis, provides a highly enantioenriched compound.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNpt0c1uEzEQAGALgWgoHHgB5AtIHBY89v7lGIVSqq5KpIaz5XVmE4fddWp7W5YH4XlxlVUjIU6jkb8Zj2YIeQvsEzAOn_eKpZwDK5-RGWScJRnw_DmZMcZ4UpS5OCOvvN_HNOUlvCRnkBVZBkLMyJ-LXvXBWI8t6mDukd6OfdihN57aht6gcnQih8EhXdruYId-Q-uRLvzYdRic0XQxBKtVUO34WLh2ZrtFh_-q1c4GeyQPJuzo0jg9tMq1I13ZGM3vWFKZ7S68Ji8a1Xp8M8Vz8uPrxXr5Lam-X14tF1WiRAkhQSwwVYVIGU8bIVgBKSt4U6dz4HEHJVeQi02ewjybCwG1aATEyqwuc643Khfn5MOx78HZuwF9kJ3xGttW9WgHL_MiY0IULMKPR6id9d5hIw_OdMqNEph8PIJ8OkK076amQ93h5iSnrUfwfgLKa9U2TvXa-JOLv5Y58OiSozM-4K-nd-V-xsFEkcn16lZ-qaBKry_n8ubUV2kv93Zwfdzdfwb8C2-cqz4</recordid><startdate>20050316</startdate><enddate>20050316</enddate><creator>Kawasaki, Tsuneomi</creator><creator>Sato, Mirai</creator><creator>Ishiguro, Saori</creator><creator>Saito, Takahiro</creator><creator>Morishita, Yosuke</creator><creator>Sato, Itaru</creator><creator>Nishino, Hideo</creator><creator>Inoue, Yoshihisa</creator><creator>Soai, Kenso</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050316</creationdate><title>Enantioselective Synthesis of Near Enantiopure Compound by Asymmetric Autocatalysis Triggered by Asymmetric Photolysis with Circularly Polarized Light</title><author>Kawasaki, Tsuneomi ; Sato, Mirai ; Ishiguro, Saori ; Saito, Takahiro ; Morishita, Yosuke ; Sato, Itaru ; Nishino, Hideo ; Inoue, Yoshihisa ; Soai, Kenso</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-ee7e4a734024f330714072fb491251282a163d641959331b3f31a385b862cda63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kawasaki, Tsuneomi</creatorcontrib><creatorcontrib>Sato, Mirai</creatorcontrib><creatorcontrib>Ishiguro, Saori</creatorcontrib><creatorcontrib>Saito, Takahiro</creatorcontrib><creatorcontrib>Morishita, Yosuke</creatorcontrib><creatorcontrib>Sato, Itaru</creatorcontrib><creatorcontrib>Nishino, Hideo</creatorcontrib><creatorcontrib>Inoue, Yoshihisa</creatorcontrib><creatorcontrib>Soai, Kenso</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kawasaki, Tsuneomi</au><au>Sato, Mirai</au><au>Ishiguro, Saori</au><au>Saito, Takahiro</au><au>Morishita, Yosuke</au><au>Sato, Itaru</au><au>Nishino, Hideo</au><au>Inoue, Yoshihisa</au><au>Soai, Kenso</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of Near Enantiopure Compound by Asymmetric Autocatalysis Triggered by Asymmetric Photolysis with Circularly Polarized Light</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2005-03-16</date><risdate>2005</risdate><volume>127</volume><issue>10</issue><spage>3274</spage><epage>3275</epage><pages>3274-3275</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>Right- and left-handed circularly polarized light (CPL) has been proposed as one of the origins of homochirality of biomolecules. However, the enantiomeric excess induced by CPL has been only very low (<2% ee). We found the unprecedented example of asymmetric autocatalysis triggered directly by a chiral physical factor, that is, right- and left-handed CPL, leading to a near enantiopure compound. Asymmetric photolysis of racemic pyrimidyl alkanol by r-CPL irradiation followed by asymmetric autocatalysis affords (R)-pyrimidyl alkanol with >99.5% ee. On the other hand, irradiation with l-CPL affords (S)-pyrimidyl alkanol with >99.5% ee. Thus, chiral physical power, such as CPL, in conjunction with asymmetric autocatalysis, provides a highly enantioenriched compound.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15755133</pmid><doi>10.1021/ja0422108</doi><tpages>2</tpages></addata></record> |
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| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Enantioselective Synthesis of Near Enantiopure Compound by Asymmetric Autocatalysis Triggered by Asymmetric Photolysis with Circularly Polarized Light |
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