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手性螺环哌啶的铱催化环缩合立体选择性合成。

Stereoselective Synthesis of Piperidines by Iridium-Catalyzed Cyclocondensation.

机构信息

Laboratorium für Organische Chemie, HCI H335, Eidgenössische Technische Hochschule Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.

出版信息

Angew Chem Int Ed Engl. 2017 Sep 11;56(38):11515-11519. doi: 10.1002/anie.201706374. Epub 2017 Aug 7.

DOI:10.1002/anie.201706374
PMID:28731546
Abstract

An iridium-catalyzed cyclocondensation of amino alcohols and aldehydes is reported. Intramolecular allylic substitution by an enamine intermediate and subsequent in situ reduction furnishes 3,4-disubstituted piperidines with high enantiospecificity and good diastereoselectivity. The modular approach and the broad functional group tolerance provide access to diverse piperidine derivatives, which were further functionalized to give a versatile set of products.

摘要

报道了铱催化的氨基醇和醛的环缩合反应。烯胺中间体的分子内烯丙基取代以及随后的原位还原，以高对映选择性和良好的非对映选择性得到 3,4-二取代的哌啶。这种模块化方法和广泛的官能团容忍性为获得各种哌啶衍生物提供了途径，这些衍生物进一步官能化得到了一组多功能的产物。

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