分子内氢化物加成到吡啶盐中：获得对映纯二氢吡啶酮的新途径。

Intramolecular hydride addition to pyridinium salts: new routes to enantiopure dihydropyridones.

机构信息

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.

出版信息

Org Lett. 2011 Apr 15;13(8):2074-7. doi: 10.1021/ol200478p. Epub 2011 Mar 18.

DOI:10.1021/ol200478p

Abstract

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.

摘要

将一个简单的二取代吡啶转化为带有一个环外羟基的吡啶翁离子，并将其保护为硅烷，当使用氟离子作为亲核试剂时，能够发生分子内氢转移反应。该加成反应具有区域和立体选择性，并且当在该序列中使用手性纯吡啶衍生物时，能够形成对映纯二氢吡啶酮。杂环产物具有丰富的功能，可用于进一步的衍生化反应和后续的衍生化。