A Novel Enantioselective Alkylation and Its Application to the Synthesis of an Anticancer Agent
A novel enantioselective alkylation of double benzylic substrates with secondary electrophiles is reported. A simple norephedrine-based chiral ligand was synthesized that gives alkylation product in 95% yield and 95% ee. A unique water effect on the enantioselectivity was unveiled. Good to excellent...
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| Veröffentlicht in: | Journal of organic chemistry 2003-06, Vol.68 (12), p.4984-4987 |
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| container_end_page | 4987 |
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| container_issue | 12 |
| container_start_page | 4984 |
| container_title | Journal of organic chemistry |
| container_volume | 68 |
| creator | Kuo, Shen-Chun Chen, Frank Hou, Donald Kim-Meade, Agnes Bernard, Charles Liu, Jinchu Levy, Stacy Wu, George G |
| description | A novel enantioselective alkylation of double benzylic substrates with secondary electrophiles is reported. A simple norephedrine-based chiral ligand was synthesized that gives alkylation product in 95% yield and 95% ee. A unique water effect on the enantioselectivity was unveiled. Good to excellent ee values were obtained with a number of double benzylic substrates and secondary electrophiles. This novel reaction has been applied to the synthesis of a promising anticancer agent. |
| doi_str_mv | 10.1021/jo034380t |
| format | Article |
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A simple norephedrine-based chiral ligand was synthesized that gives alkylation product in 95% yield and 95% ee. A unique water effect on the enantioselectivity was unveiled. Good to excellent ee values were obtained with a number of double benzylic substrates and secondary electrophiles. 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Org. Chem</addtitle><description>A novel enantioselective alkylation of double benzylic substrates with secondary electrophiles is reported. A simple norephedrine-based chiral ligand was synthesized that gives alkylation product in 95% yield and 95% ee. A unique water effect on the enantioselectivity was unveiled. Good to excellent ee values were obtained with a number of double benzylic substrates and secondary electrophiles. This novel reaction has been applied to the synthesis of a promising anticancer agent.</description><subject>Alkylation</subject><subject>Antineoplastic Agents - analysis</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Indicators and Reagents</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Piperidines - analysis</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - pharmacology</subject><subject>Preparations and properties</subject><subject>Pyridines - analysis</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - pharmacology</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE9v1DAQxS0Eard_DnwB5AuVOATGsRPHx2jV0kIFlVoEN8txJm1ar7O1vRX77fFqV90LcxnpzU9Pbx4h7xl8ZlCyL48TcMEbSG_IjFUlFLUC8ZbMAMqy4GXND8lRjI-Qp6qqA3LISqmgZnJGdEt_TC_o6Lk3Po1TRIc2jS9IW_e0diZLnhrf06sUabtcutFutTTR9ID0du3zimOk05A52mYTa7zFQNt79OmEvBuMi3i628fk18X53fyyuP759WreXheGS5UK2bO-aZCj6oQUnR1EbcUAfcMHJTe_cRRWVA10qhE1Y50CyWyP0CtWWgX8mJxtfZdhel5hTHoxRovOGY_TKmrJuZJCsQx-2oI2TDEGHPQyjAsT1pqB3rSpX9vM7Ied6apbYL8nd_Vl4OMOMNEaN4T8-Rj3nGikqmDDFVtujAn_vt5NeNK15LLSdze3ev7tz3clf891s_c1NuY8q-Bzd_8J-A-7p5b5</recordid><startdate>20030613</startdate><enddate>20030613</enddate><creator>Kuo, Shen-Chun</creator><creator>Chen, Frank</creator><creator>Hou, Donald</creator><creator>Kim-Meade, Agnes</creator><creator>Bernard, Charles</creator><creator>Liu, Jinchu</creator><creator>Levy, Stacy</creator><creator>Wu, George G</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20030613</creationdate><title>A Novel Enantioselective Alkylation and Its Application to the Synthesis of an Anticancer Agent</title><author>Kuo, Shen-Chun ; Chen, Frank ; Hou, Donald ; Kim-Meade, Agnes ; Bernard, Charles ; Liu, Jinchu ; Levy, Stacy ; Wu, George G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-7d1d88e3e9b474bcf46c4f0d83f9734383e4c4580b984611b9071cde0d912c903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Alkylation</topic><topic>Antineoplastic Agents - analysis</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Indicators and Reagents</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Piperidines - analysis</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - pharmacology</topic><topic>Preparations and properties</topic><topic>Pyridines - analysis</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - pharmacology</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kuo, Shen-Chun</creatorcontrib><creatorcontrib>Chen, Frank</creatorcontrib><creatorcontrib>Hou, Donald</creatorcontrib><creatorcontrib>Kim-Meade, Agnes</creatorcontrib><creatorcontrib>Bernard, Charles</creatorcontrib><creatorcontrib>Liu, Jinchu</creatorcontrib><creatorcontrib>Levy, Stacy</creatorcontrib><creatorcontrib>Wu, George G</creatorcontrib><collection>Istex</collection><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>Kuo, Shen-Chun</au><au>Chen, Frank</au><au>Hou, Donald</au><au>Kim-Meade, Agnes</au><au>Bernard, Charles</au><au>Liu, Jinchu</au><au>Levy, Stacy</au><au>Wu, George G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Novel Enantioselective Alkylation and Its Application to the Synthesis of an Anticancer Agent</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-06-13</date><risdate>2003</risdate><volume>68</volume><issue>12</issue><spage>4984</spage><epage>4987</epage><pages>4984-4987</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A novel enantioselective alkylation of double benzylic substrates with secondary electrophiles is reported. A simple norephedrine-based chiral ligand was synthesized that gives alkylation product in 95% yield and 95% ee. A unique water effect on the enantioselectivity was unveiled. Good to excellent ee values were obtained with a number of double benzylic substrates and secondary electrophiles. This novel reaction has been applied to the synthesis of a promising anticancer agent.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12790617</pmid><doi>10.1021/jo034380t</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2003-06, Vol.68 (12), p.4984-4987 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Alkylation Antineoplastic Agents - analysis Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Catalysis Chemistry Combinatorial Chemistry Techniques Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Indicators and Reagents Molecular Structure Organic chemistry Piperidines - analysis Piperidines - chemical synthesis Piperidines - pharmacology Preparations and properties Pyridines - analysis Pyridines - chemical synthesis Pyridines - pharmacology Stereoisomerism |
| title | A Novel Enantioselective Alkylation and Its Application to the Synthesis of an Anticancer Agent |
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