Intramolecular Hydride Addition to Pyridinium Salts: New Routes to Enantiopure Dihydropyridones

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• 作者：Timothy J. Donohoe ; Matthew J. Connolly ; Akshat H. Rathi ; Lesley Walton
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：April 15, 2011
• 年：2011
• 卷：13
• 期：8
• 页码：2074-2077
• 全文大小：786K
• 年卷期：v.13,no.8(April 15, 2011)
• ISSN：1523-7052

文摘

The transformation of a simple disubstituted pyridine into a pyridinium ion bearing an exocyclic hydroxyl group, protected as a silane, enabled an intramolecular hydride transfer reaction to take place when fluoride was used as a nucleophile. The addition was both regio- and stereoselective and enabled the formation of enantiopure dihydropyridones when enantiopure pyridine derivatives were used in this sequence. The heterocyclic products contain ample functionality for further elaboration reactions and subsequent derivatization.