Karmakar, Ananta 
; Maji, Tapan ; Wittmann, Sebastian ; Reiser, Oliver
Alternative Links zum Volltext:DOIVerlag
| Dokumentenart: | Artikel |
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| Titel eines Journals oder einer Zeitschrift: | Chemistry – A European Journal |
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| Verlag: | WILEY-V C H VERLAG GMBH |
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| Ort der Veröffentlichung: | WEINHEIM |
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| Band: | 17 |
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| Nummer des Zeitschriftenheftes oder des Kapitels: | 39 |
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| Seitenbereich: | S. 11024-11029 |
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| Datum: | 2011 |
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| Institutionen: | Chemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
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| Identifikationsnummer: | | Wert | Typ |
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| 10.1002/chem.201101299 | DOI |
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| Stichwörter / Keywords: | CATALYTIC ASYMMETRIC ALDOL; L-PROLINE; AQUEOUS-MEDIA; ZINC-PROLINE; AMINO-ACID; MICHAEL ADDITION; INCREASED REACTIVITY; VERSATILE CATALYSTS; ORGANIC-MOLECULES; ENAMINE CATALYSIS; aldol reaction; aldehydes; cobalt; diastereoselectivity; ketones |
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| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
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| Status: | Veröffentlicht |
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| Begutachtet: | Ja, diese Version wurde begutachtet |
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| An der Universität Regensburg entstanden: | Ja |
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| Dokumenten-ID: | 64603 |
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Web of Science
Zusammenfassung
The CoCl2/L-proline (1:2) system was found to be an excellent catalyst for direct aldol reactions. Excellent yields (up to 93%) and a significant improvement in diastereoselectivity (anti/syn up to 45:1) as well as enantioselectivity (up to more than 99% ee) compared with using proline as the sole catalyst were observed. This catalyst system was successfully applied to both cyclic and acyclic ...
Zusammenfassung
The CoCl2/L-proline (1:2) system was found to be an excellent catalyst for direct aldol reactions. Excellent yields (up to 93%) and a significant improvement in diastereoselectivity (anti/syn up to 45:1) as well as enantioselectivity (up to more than 99% ee) compared with using proline as the sole catalyst were observed. This catalyst system was successfully applied to both cyclic and acyclic ketones in combination with aromatic and aliphatic aldehydes. In situ chelation of CoCl2 and proline (1:2) is proposed to promote the reaction through a six-membered Zimmermann-Traxler type transition state involving the positioning of proline-enamine and the aldehyde through chelation to Co-II.
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