Dynamic kinetic resolution and desymmetrization processes:: A straightforward methodology for the enantioselective synthesis of piperidines
Dynamic kinetic resolution and desymmetrization processes:: A straightforward methodology for the enantioselective synthesis of piperidines
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DOI：
10.1002/chem.200600420
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发表时间：
2006-10-16
影响因子：
4.3
通讯作者：
Bosch, Joan
中科院分区：
文献类型：
--
作者：
Amat, Mercedes;Bassas, Oriol;Bosch, Joan
报道了一种合成对映体纯的多取代哌啶的简单方法。它涉及直接生成手性非外消旋恶唑并[3，2-a]哌啶酮内酰胺，其已经在杂环上引入碳取代基，随后除去手性助剂。关键步骤是（R）-苯基甘氨醇或其他氨基醇与外消旋或前手性δ-氧代（二）酸衍生物在高度立体选择性过程中的环化缩合反应，该过程涉及非对映异构或对映异构酯基的动态动力学拆分和/或去对称化。
A straightforward procedure for the synthesis of enantiopure polysubstituted piperidines is reported. It involves the direct generation of chiral non-racemic oxazolo[3,2-a]piperidone lactams that already incorporate carbon substituents on the heterocyclic ring and the subsequent removal of the chiral auxiliary. The key step is a cyclocondensation reaction of (R)-phenylglycinol or other amino alcohols with racemic or prochiral delta-oxo (di)acid derivatives in highly stereoselective processes involving dynamic kinetic resolution and/or desymmetrization of diastereotopic or enantiotopic ester groups.