A Highly Enantioselective Access to Tetrahydroisoquinoline and β-Carboline Alkaloids with Simple Noyori-Type Catalysts in Aqueous Media
Silver enhancement: A very convenient modified protocol for the enantioselective transfer hydrogenation of dihydroisoquinoline skeletons under aqueous conditions is reported. Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme)...
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Veröffentlicht in: | Chemistry : a European journal 2009-12, Vol.15 (47), p.12963-12967 |
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creator | Evanno, Laurent Ormala, Joel Pihko, Petri M. |
description | Silver enhancement: A very convenient modified protocol for the enantioselective transfer hydrogenation of dihydroisoquinoline skeletons under aqueous conditions is reported. Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme). The protocol was used in a very short synthesis of the alkaloids (S)‐harmicine and (S)‐crispine. |
doi_str_mv | 10.1002/chem.200902289 |
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Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme). The protocol was used in a very short synthesis of the alkaloids (S)‐harmicine and (S)‐crispine.</description><subject>alkaloids</subject><subject>asymmetric synthesis</subject><subject>catalysis</subject><subject>imines</subject><subject>lanthanides</subject><subject>transfer hydrogenation</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqFkMGO0zAQhi0EYsvClSPyjVOKHdd2fIxK2a66uwhRxNFynAk168RdO2XJG-zz8CA8E6lSLdw4jTT6_k8zP0KvKZlTQvJ3dgftPCdEkTwv1BM0ozynGZOCP0UzohYyE5ypM_Qipe9kxARjz9EZVQVXKhcz9FDitfu28wNedabrXUjgwfbuB-DSWkgJ9wFvoY9mN9QxuBTuDq4L3nWATVfj37-ypYnVtCj9rfHB1Qnfu36HP7t27wHfhCFEl22HPeCl6Y0fUp-w63B5d4BwSPgaamdeomeN8QleneY5-vJhtV2us6uPF5fL8iqzizxXmay4ZEQsCFhaN5YLoIUAqIuiqnJOGkOoKSi3pqaWjG9SVkEjmWgqBYoayc7R28m7j-MrkHrdumTBe9Mdj9GSLagUtOAjOZ9IG0NKERq9j641cdCU6GP5-li-fix_DLw5qQ9VC_Vf_NT2CKgJuHcehv_o9HK9uv5Xnk1Zl3r4-Zg18VYLySTXX28u9Pv1hqhPm41m7A9b1KNl</recordid><startdate>20091207</startdate><enddate>20091207</enddate><creator>Evanno, Laurent</creator><creator>Ormala, Joel</creator><creator>Pihko, Petri M.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20091207</creationdate><title>A Highly Enantioselective Access to Tetrahydroisoquinoline and β-Carboline Alkaloids with Simple Noyori-Type Catalysts in Aqueous Media</title><author>Evanno, Laurent ; Ormala, Joel ; Pihko, Petri M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4229-7b5730640ec1dfc56e186eed88bb250fa01a815cad1c019813bef736fb9e91a73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>alkaloids</topic><topic>asymmetric synthesis</topic><topic>catalysis</topic><topic>imines</topic><topic>lanthanides</topic><topic>transfer hydrogenation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Evanno, Laurent</creatorcontrib><creatorcontrib>Ormala, Joel</creatorcontrib><creatorcontrib>Pihko, Petri M.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Evanno, Laurent</au><au>Ormala, Joel</au><au>Pihko, Petri M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Highly Enantioselective Access to Tetrahydroisoquinoline and β-Carboline Alkaloids with Simple Noyori-Type Catalysts in Aqueous Media</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry - A European Journal</addtitle><date>2009-12-07</date><risdate>2009</risdate><volume>15</volume><issue>47</issue><spage>12963</spage><epage>12967</epage><pages>12963-12967</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Silver enhancement: A very convenient modified protocol for the enantioselective transfer hydrogenation of dihydroisoquinoline skeletons under aqueous conditions is reported. Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme). The protocol was used in a very short synthesis of the alkaloids (S)‐harmicine and (S)‐crispine.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>19859926</pmid><doi>10.1002/chem.200902289</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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source | Wiley Online Library Journals Frontfile Complete |
subjects | alkaloids asymmetric synthesis catalysis imines lanthanides transfer hydrogenation |
title | A Highly Enantioselective Access to Tetrahydroisoquinoline and β-Carboline Alkaloids with Simple Noyori-Type Catalysts in Aqueous Media |
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