Enzyme-Catalyzed Kinetic Resolution of 1,3-anti-Diol Monoesters - Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3-anti-Diols
Candida antarctica Lipase B (CALB) catalyzed the highly enantioselective acetylation of 1,3‐anti‐diol monoesters which have been obtained through a zirconium‐catalyzed aldol‐Tishchenko reaction. The product 1,3‐anti‐diol diesters were formed in yields close to 50 % and >98 % ee. Separation from t...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2007-06, Vol.2007 (18), p.2958-2963 |
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| container_title | European Journal of Organic Chemistry |
| container_volume | 2007 |
| creator | Jakob, Florian Schneider, Christoph |
| description | Candida antarctica Lipase B (CALB) catalyzed the highly enantioselective acetylation of 1,3‐anti‐diol monoesters which have been obtained through a zirconium‐catalyzed aldol‐Tishchenko reaction. The product 1,3‐anti‐diol diesters were formed in yields close to 50 % and >98 % ee. Separation from the unreactive enantiomers and subsequent hydrolysis furnished both enantiomers of unsymmetrically substituted 1,3‐anti‐diols in high optical purities. Alternatively, the kinetic resolution process can be performed on the free 1,3‐anti‐diols even more rapidly with equally good results. A slow acyl migration during the reaction slightly deteriorated the enantiomeric excess of the unreactive enantiomers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007) |
| doi_str_mv | 10.1002/ejoc.200700096 |
| format | Article |
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The product 1,3‐anti‐diol diesters were formed in yields close to 50 % and >98 % ee. Separation from the unreactive enantiomers and subsequent hydrolysis furnished both enantiomers of unsymmetrically substituted 1,3‐anti‐diols in high optical purities. Alternatively, the kinetic resolution process can be performed on the free 1,3‐anti‐diols even more rapidly with equally good results. A slow acyl migration during the reaction slightly deteriorated the enantiomeric excess of the unreactive enantiomers. (© Wiley‐VCH Verlag GmbH & Co. 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KGaA, 69451 Weinheim, Germany, 2007)</description><subject>1,3‐Diols</subject><subject>3-Diols</subject><subject>Aldol-Tishchenko reaction</subject><subject>Enzyme catalysis</subject><subject>Kinetic resolution</subject><subject>Lipase</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNqFkN1OGzEQhVeolaDQ2177AeowXic2vqzCNtDy25afO8txxmC6ayPbEV0eqU_JhhTUXnVuZjRzvjnSqaoPDEYMoN7Fu2hHNYAEACU2qi0GSlEQCt4M85iPKVP8erN6l_Pds0Swrep3Ex77DunUFNP2j7ggX33A4i35hjm2y-JjINER9pFTE4qn-z625DiGiLlgyoSSxjlvPYZCzhLem2RemCasiNhh8ta0bU8O_M3t0JowLG4HKxMW5CLkvuuwvGi-L-e5-LIsw_0f07xTvXWmzfj-T9-uLj43P6YH9Oh0djj9dEQtV1zQMdaLibBuVbxmc6Yk7gluDYIbS-uME5M5CAAm5SCTYGojnVQwd4taGsG3q9H6r00x54RO3yffmdRrBnqVtF4lrV-THgC1Bh58i_1_1Lr5cjr9m6Vr1g9x_nplTfqpheRyoq9OZvqSw_nl3vFMc_4EUkqVwA</recordid><startdate>200706</startdate><enddate>200706</enddate><creator>Jakob, Florian</creator><creator>Schneider, Christoph</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200706</creationdate><title>Enzyme-Catalyzed Kinetic Resolution of 1,3-anti-Diol Monoesters - Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3-anti-Diols</title><author>Jakob, Florian ; Schneider, Christoph</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3936-4e2d56cfffff321b197e863cae0f47cfaf65b06001776cf70a2a7f790bfd27a63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>1,3‐Diols</topic><topic>3-Diols</topic><topic>Aldol-Tishchenko reaction</topic><topic>Enzyme catalysis</topic><topic>Kinetic resolution</topic><topic>Lipase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jakob, Florian</creatorcontrib><creatorcontrib>Schneider, Christoph</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jakob, Florian</au><au>Schneider, Christoph</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enzyme-Catalyzed Kinetic Resolution of 1,3-anti-Diol Monoesters - Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3-anti-Diols</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. 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| ispartof | European Journal of Organic Chemistry, 2007-06, Vol.2007 (18), p.2958-2963 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ejoc_200700096 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 1,3‐Diols 3-Diols Aldol-Tishchenko reaction Enzyme catalysis Kinetic resolution Lipase |
| title | Enzyme-Catalyzed Kinetic Resolution of 1,3-anti-Diol Monoesters - Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3-anti-Diols |
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