Catalytic, Asymmetric Inverse Electron Demand Hetero Diels-Alder Reactions of o-Benzoquinone Derivatives and Ketene Enolates
| Autor: | Daniel H. Paull, Jamison Wolfer, James W. Grebinski, Anthony Weatherwax, Thomas Lectka |
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| Jazyk: | German<br />English<br />French |
| Rok vydání: | 2007 |
| Předmět: | |
| Zdroj: | CHIMIA, Vol 61, Iss 5 (2007) |
| Druh dokumentu: | article |
| ISSN: | 0009-4293 2673-2424 |
| DOI: | 10.2533/chimia.2007.240 |
| Popis: | We present an array of [4+2] cycloaddition reactions between ketene enolates, catalytically derived from acid chlorides and cinchona alkaloid nucleophilic catalysts in the presence of stoichiometric base, and o-benzoquinone derivatives. These cycloaddition reactions proceed with excellent stereochemical control (up to >99% ee). In fact, for both the o-benzoquinone imide and the o-benzoquinone diimide manifolds, these Diels-Alder reactions occurred with uniformly >99% ee. The wide scope of this methodology provides access to a diverse range of biologically and synthetically useful chiral products, including ?-hydroxyesters, non-natural ?-amino acids, quinoxalinones, and many others, all with remarkable, catalytic control of regio- and stereochemistry. |
| Databáze: | Directory of Open Access Journals |
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