Enantioselective 1,4-Addition Reactions of Diphenyl Phosphite to Nitroalkenes Catalyzed by an Axially Chiral Guanidine
A highly enantioselective 1,4-addition reaction of nitroalkenes with diphenyl phosphite was successfully accomplished using a newly developed axially chiral guainidine catalyst. A broad range of nitroalkenes, bearing not only aromatic but also aliphatic substituents, is applicable to the present ena...
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| Veröffentlicht in: | Journal of the American Chemical Society 2007-11, Vol.129 (46), p.14112-14113 |
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| container_end_page | 14113 |
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| container_issue | 46 |
| container_start_page | 14112 |
| container_title | Journal of the American Chemical Society |
| container_volume | 129 |
| creator | Terada, Masahiro Ikehara, Takashi Ube, Hitoshi |
| description | A highly enantioselective 1,4-addition reaction of nitroalkenes with diphenyl phosphite was successfully accomplished using a newly developed axially chiral guainidine catalyst. A broad range of nitroalkenes, bearing not only aromatic but also aliphatic substituents, is applicable to the present enantioselective reaction. The method provides an efficient protocol to synthesize enantioenriched β-amino phosphonate derivatives of biological and pharmaceutical importance. |
| doi_str_mv | 10.1021/ja0746619 |
| format | Article |
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Am. Chem. Soc</addtitle><description>A highly enantioselective 1,4-addition reaction of nitroalkenes with diphenyl phosphite was successfully accomplished using a newly developed axially chiral guainidine catalyst. A broad range of nitroalkenes, bearing not only aromatic but also aliphatic substituents, is applicable to the present enantioselective reaction. The method provides an efficient protocol to synthesize enantioenriched β-amino phosphonate derivatives of biological and pharmaceutical importance.</description><subject>Alkenes - chemical synthesis</subject><subject>Catalysis</subject><subject>Guanidine - chemistry</subject><subject>Models, Chemical</subject><subject>Nitro Compounds - chemical synthesis</subject><subject>Organophosphonates - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMFuEzEQhi0EoqFw4AWQLyAhseDxeu3dYwhtihQggnK2nN1ZxaljB9tbdXn6bpWoXDjNjP3pH81HyGtgH4Fx-LQzTAkpoXlCZlBxVlTA5VMyY4zxQtWyPCMvUtpNo-A1PCdnoBrJGiZm5PbCG59tSOiwzfYWKXwQxbzr7PTo6U807UOTaOjpF3vYoh8dXW9DOmxtRpoD_W5zDMbdoMdEFyYbN_7Fjm5Gajyd31nj3EgXWxuNo8vBeNtZjy_Js964hK9O9Zz8vry4XlwVqx_Lr4v5qjACVC6gb3nf8U3JhQDTKFWJDSJnUE0XYl1JqTiytpSd6MqS9w20houmbIDVIIGX5-TdMfcQw58BU9Z7m1p0zngMQ9KynoIqJSbw_RFsY0gpYq8P0e5NHDUw_SBZP0qe2Den0GGzx-4febI6AcURsCnj3eO_iTdaqlJV-nr9S1_x6tuqWX_Wy4l_e-RNm_QuDNFPTv6z-B6XrZEJ</recordid><startdate>20071121</startdate><enddate>20071121</enddate><creator>Terada, Masahiro</creator><creator>Ikehara, Takashi</creator><creator>Ube, Hitoshi</creator><general>American Chemical Society</general><scope>BSCLL</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>20071121</creationdate><title>Enantioselective 1,4-Addition Reactions of Diphenyl Phosphite to Nitroalkenes Catalyzed by an Axially Chiral Guanidine</title><author>Terada, Masahiro ; Ikehara, Takashi ; Ube, Hitoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a417t-1fc2fd2b32441a97754bee2015512e856672e0c36d4d332f91ca2493910816123</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Alkenes - chemical synthesis</topic><topic>Catalysis</topic><topic>Guanidine - chemistry</topic><topic>Models, Chemical</topic><topic>Nitro Compounds - chemical synthesis</topic><topic>Organophosphonates - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Terada, Masahiro</creatorcontrib><creatorcontrib>Ikehara, Takashi</creatorcontrib><creatorcontrib>Ube, Hitoshi</creatorcontrib><collection>Istex</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 the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Terada, Masahiro</au><au>Ikehara, Takashi</au><au>Ube, Hitoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective 1,4-Addition Reactions of Diphenyl Phosphite to Nitroalkenes Catalyzed by an Axially Chiral Guanidine</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. 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| fulltext | fulltext |
| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2007-11, Vol.129 (46), p.14112-14113 |
| issn | 0002-7863 1520-5126 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68512574 |
| source | MEDLINE; ACS Publications |
| subjects | Alkenes - chemical synthesis Catalysis Guanidine - chemistry Models, Chemical Nitro Compounds - chemical synthesis Organophosphonates - chemistry |
| title | Enantioselective 1,4-Addition Reactions of Diphenyl Phosphite to Nitroalkenes Catalyzed by an Axially Chiral Guanidine |
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