Catalytic Asymmetric Syntheses of α-Amino and α-Hydroxyl Acid Derivatives
Herein we report the first room temperature Heck reaction of aryl bromides and CH2C(NHP)CO2Me (P = Boc or CBz) to form ArCHC(NHP)CO2Me, which are then used for the asymmetric syntheses of α-amino acids. We also report the first syntheses of ArCHC(OCOAr1)CO2Me (Ar1 = Ph, 4-Cl−Ph) from ArBr and CH2...
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| Veröffentlicht in: | Journal of organic chemistry 2009-05, Vol.74 (10), p.3993-3996 |
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| container_end_page | 3996 |
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| container_issue | 10 |
| container_start_page | 3993 |
| container_title | Journal of organic chemistry |
| container_volume | 74 |
| creator | Han, Xiaojun Jiang, Xiang-Jun Civiello, Rita L Degnan, Andrew P Chaturvedula, Prasad V Macor, John E Dubowchik, Gene M |
| description | Herein we report the first room temperature Heck reaction of aryl bromides and CH2C(NHP)CO2Me (P = Boc or CBz) to form ArCHC(NHP)CO2Me, which are then used for the asymmetric syntheses of α-amino acids. We also report the first syntheses of ArCHC(OCOAr1)CO2Me (Ar1 = Ph, 4-Cl−Ph) from ArBr and CH2C(OCOAr1)CO2Me by the Heck reaction and subsequent successful asymmetric hydrogenation to afford α-hydroxyl esters in excellent chemical yields and good-to-excellent enantioselectivities. |
| doi_str_mv | 10.1021/jo900368k |
| format | Article |
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We also report the first syntheses of ArCHC(OCOAr1)CO2Me (Ar1 = Ph, 4-Cl−Ph) from ArBr and CH2C(OCOAr1)CO2Me by the Heck reaction and subsequent successful asymmetric hydrogenation to afford α-hydroxyl esters in excellent chemical yields and good-to-excellent enantioselectivities.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo900368k</identifier><identifier>PMID: 19378930</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Amino Acids - chemical synthesis ; Amino Acids - chemistry ; Bromides - chemistry ; Catalysis ; Chemistry ; Esters - chemical synthesis ; Esters - chemistry ; Exact sciences and technology ; Hydroxides - chemistry ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties ; Stereoisomerism ; Substrate Specificity ; Temperature</subject><ispartof>Journal of organic chemistry, 2009-05, Vol.74 (10), p.3993-3996</ispartof><rights>Copyright © 2009 American Chemical Society</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a343t-243acd251e7d3d6d727027483c78604b3f75b1eef18f778ff687397056433c133</citedby><cites>FETCH-LOGICAL-a343t-243acd251e7d3d6d727027483c78604b3f75b1eef18f778ff687397056433c133</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/jo900368k$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo900368k$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21490814$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19378930$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Han, Xiaojun</creatorcontrib><creatorcontrib>Jiang, Xiang-Jun</creatorcontrib><creatorcontrib>Civiello, Rita L</creatorcontrib><creatorcontrib>Degnan, Andrew P</creatorcontrib><creatorcontrib>Chaturvedula, Prasad V</creatorcontrib><creatorcontrib>Macor, John E</creatorcontrib><creatorcontrib>Dubowchik, Gene M</creatorcontrib><title>Catalytic Asymmetric Syntheses of α-Amino and α-Hydroxyl Acid Derivatives</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Herein we report the first room temperature Heck reaction of aryl bromides and CH2C(NHP)CO2Me (P = Boc or CBz) to form ArCHC(NHP)CO2Me, which are then used for the asymmetric syntheses of α-amino acids. We also report the first syntheses of ArCHC(OCOAr1)CO2Me (Ar1 = Ph, 4-Cl−Ph) from ArBr and CH2C(OCOAr1)CO2Me by the Heck reaction and subsequent successful asymmetric hydrogenation to afford α-hydroxyl esters in excellent chemical yields and good-to-excellent enantioselectivities.</description><subject>Amino Acids - chemical synthesis</subject><subject>Amino Acids - chemistry</subject><subject>Bromides - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Esters - chemical synthesis</subject><subject>Esters - chemistry</subject><subject>Exact sciences and technology</subject><subject>Hydroxides - chemistry</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Substrate Specificity</subject><subject>Temperature</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtKw0AUhgdRbK0ufAHJRsFFdO4zWYZ6qVhwoa7DdDKDU3OpM0kxj-WL-EymNLQbz-acAx__Dx8A5wjeIIjR7bJOICRcfh6AMWIYxjyB9BCMIcQ4JpiTETgJYQn7YYwdgxFKiJAJgWPwPFWNKrrG6SgNXVmaxvfna1c1HyaYENU2-v2J09JVdaSqfPPMutzX310Rpdrl0Z3xbq0atzbhFBxZVQRzNuwJeH-4f5vO4vnL49M0nceKUNLEmBKlc8yQETnJeS6wgFhQSbSQHNIFsYItkDEWSSuEtJZLQRIBGaeEaETIBFxtc1e-_mpNaLLSBW2KQlWmbkPGBUaUJbgHr7eg9nUI3ths5V2pfJchmG3MZTtzPXsxhLaL0uR7clDVA5cDoIJWhfWq0i7suL4ygRLRPad06PNbX_Uu_in8Axc9gXg</recordid><startdate>20090515</startdate><enddate>20090515</enddate><creator>Han, Xiaojun</creator><creator>Jiang, Xiang-Jun</creator><creator>Civiello, Rita L</creator><creator>Degnan, Andrew P</creator><creator>Chaturvedula, Prasad V</creator><creator>Macor, John E</creator><creator>Dubowchik, Gene M</creator><general>American Chemical Society</general><scope>IQODW</scope><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>20090515</creationdate><title>Catalytic Asymmetric Syntheses of α-Amino and α-Hydroxyl Acid Derivatives</title><author>Han, Xiaojun ; Jiang, Xiang-Jun ; Civiello, Rita L ; Degnan, Andrew P ; Chaturvedula, Prasad V ; Macor, John E ; Dubowchik, Gene M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a343t-243acd251e7d3d6d727027483c78604b3f75b1eef18f778ff687397056433c133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Amino Acids - chemical synthesis</topic><topic>Amino Acids - chemistry</topic><topic>Bromides - chemistry</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Esters - chemical synthesis</topic><topic>Esters - chemistry</topic><topic>Exact sciences and technology</topic><topic>Hydroxides - chemistry</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><topic>Substrate Specificity</topic><topic>Temperature</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Han, Xiaojun</creatorcontrib><creatorcontrib>Jiang, Xiang-Jun</creatorcontrib><creatorcontrib>Civiello, Rita L</creatorcontrib><creatorcontrib>Degnan, Andrew P</creatorcontrib><creatorcontrib>Chaturvedula, Prasad V</creatorcontrib><creatorcontrib>Macor, John E</creatorcontrib><creatorcontrib>Dubowchik, Gene M</creatorcontrib><collection>Pascal-Francis</collection><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>Han, Xiaojun</au><au>Jiang, Xiang-Jun</au><au>Civiello, Rita L</au><au>Degnan, Andrew P</au><au>Chaturvedula, Prasad V</au><au>Macor, John E</au><au>Dubowchik, Gene M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Asymmetric Syntheses of α-Amino and α-Hydroxyl Acid Derivatives</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2009-05-15</date><risdate>2009</risdate><volume>74</volume><issue>10</issue><spage>3993</spage><epage>3996</epage><pages>3993-3996</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Herein we report the first room temperature Heck reaction of aryl bromides and CH2C(NHP)CO2Me (P = Boc or CBz) to form ArCHC(NHP)CO2Me, which are then used for the asymmetric syntheses of α-amino acids. We also report the first syntheses of ArCHC(OCOAr1)CO2Me (Ar1 = Ph, 4-Cl−Ph) from ArBr and CH2C(OCOAr1)CO2Me by the Heck reaction and subsequent successful asymmetric hydrogenation to afford α-hydroxyl esters in excellent chemical yields and good-to-excellent enantioselectivities.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>19378930</pmid><doi>10.1021/jo900368k</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2009-05, Vol.74 (10), p.3993-3996 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Amino Acids - chemical synthesis Amino Acids - chemistry Bromides - chemistry Catalysis Chemistry Esters - chemical synthesis Esters - chemistry Exact sciences and technology Hydroxides - chemistry Noncondensed benzenic compounds Organic chemistry Preparations and properties Stereoisomerism Substrate Specificity Temperature |
| title | Catalytic Asymmetric Syntheses of α-Amino and α-Hydroxyl Acid Derivatives |
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