A step-wise reduction of nonracemic α-ketoamides to α-methine amides under mild conditions
A step-wise reductive method that converts nonracemic γ-chiral α-ketoamides into amide derivatives was developed under mild conditions. The method involves a highly efficient three-step transformation including NaBH4-reduction, bromination and Pd/C hydrogenation reactions. As a consequence, a variet...
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| Veröffentlicht in: | Tetrahedron 2016-04, Vol.72 (16), p.2042-2047 |
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| container_title | Tetrahedron |
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| creator | Wang, Bing Wang, Min Jia, Tao Lou, Yazhou Liao, Jian Cao, Peng |
| description | A step-wise reductive method that converts nonracemic γ-chiral α-ketoamides into amide derivatives was developed under mild conditions. The method involves a highly efficient three-step transformation including NaBH4-reduction, bromination and Pd/C hydrogenation reactions. As a consequence, a variety of nonracemic γ-diaryl amides products were obtained in high overall yields with excellent enantiomeric specificity. The utility of the method is demonstrated through the concise formal synthesis of (+)-sertraline in good overall yield.
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| doi_str_mv | 10.1016/j.tet.2016.03.001 |
| format | Article |
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[Display omitted]</description><subject>Amides</subject><subject>Bromination</subject><subject>Derivatives</subject><subject>Enantiomeric specificity</subject><subject>Hydrogenation</subject><subject>Nonracemic</subject><subject>Reduction</subject><subject>Synthesis</subject><subject>Tetrahedrons</subject><subject>Transformations</subject><subject>Utilities</subject><subject>α-Ketoamides</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9UMtOwzAQtBBIlMIHcPORS8I6TpxUnKqKl1SJS49IlmtvhEsSF9sB8Vn8CN-Eo_bMaVejmdnZIeSaQc6AidtdHjHmRVpz4DkAOyEzVooyq0omTskMoISshALOyUUIO0gMVvAZeV3SEHGffdmA1KMZdbRuoK6lgxu80thbTX9_sneMTvXWYKDRTUCP8c0OSI_gOBj0tLedodoNxk4u4ZKctaoLeHWcc7J5uN-snrL1y-PzarnONOcQsxpMXfJSqEYZgKpGgG1ToxGoWs2LpjLbFHdRtVVdAKhCVAI0F9WibY1SwOfk5mC79-5jxBBlb4PGrlMDujFI1jABZVULkajsQNXeheCxlXtve-W_JQM5FSl3MhUppyIlcJnuJs3dQYPphU-LXgZtcdBorEcdpXH2H_UfCTp8_A</recordid><startdate>20160421</startdate><enddate>20160421</enddate><creator>Wang, Bing</creator><creator>Wang, Min</creator><creator>Jia, Tao</creator><creator>Lou, Yazhou</creator><creator>Liao, Jian</creator><creator>Cao, Peng</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20160421</creationdate><title>A step-wise reduction of nonracemic α-ketoamides to α-methine amides under mild conditions</title><author>Wang, Bing ; Wang, Min ; Jia, Tao ; Lou, Yazhou ; Liao, Jian ; Cao, Peng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c330t-70d74346a8ad0057e00b87ed6eafc3285db00195f57200a26560c3659ffdaa03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Amides</topic><topic>Bromination</topic><topic>Derivatives</topic><topic>Enantiomeric specificity</topic><topic>Hydrogenation</topic><topic>Nonracemic</topic><topic>Reduction</topic><topic>Synthesis</topic><topic>Tetrahedrons</topic><topic>Transformations</topic><topic>Utilities</topic><topic>α-Ketoamides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Bing</creatorcontrib><creatorcontrib>Wang, Min</creatorcontrib><creatorcontrib>Jia, Tao</creatorcontrib><creatorcontrib>Lou, Yazhou</creatorcontrib><creatorcontrib>Liao, Jian</creatorcontrib><creatorcontrib>Cao, Peng</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Bing</au><au>Wang, Min</au><au>Jia, Tao</au><au>Lou, Yazhou</au><au>Liao, Jian</au><au>Cao, Peng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A step-wise reduction of nonracemic α-ketoamides to α-methine amides under mild conditions</atitle><jtitle>Tetrahedron</jtitle><date>2016-04-21</date><risdate>2016</risdate><volume>72</volume><issue>16</issue><spage>2042</spage><epage>2047</epage><pages>2042-2047</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>A step-wise reductive method that converts nonracemic γ-chiral α-ketoamides into amide derivatives was developed under mild conditions. The method involves a highly efficient three-step transformation including NaBH4-reduction, bromination and Pd/C hydrogenation reactions. As a consequence, a variety of nonracemic γ-diaryl amides products were obtained in high overall yields with excellent enantiomeric specificity. The utility of the method is demonstrated through the concise formal synthesis of (+)-sertraline in good overall yield.
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| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Amides Bromination Derivatives Enantiomeric specificity Hydrogenation Nonracemic Reduction Synthesis Tetrahedrons Transformations Utilities α-Ketoamides |
| title | A step-wise reduction of nonracemic α-ketoamides to α-methine amides under mild conditions |
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