One-Step Diastereoselective Pyrrolidine Synthesis Using a Sulfinamide Annulating Reagent

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2019-10-24 DOI:10.1021/acs.orglett.9b03560

Qing Shi*, Nathaniel S. Greenwood, Mariah C. Meehan, Hyunsoo Park, Michael Galella, Bhupinder Sandhu, Purnima Khandelwal, John R. Coombs, William P. Gallagher, Carlos A. Guerrero, John Hynes Jr., T. G. Murali Dhar, Francisco Gonzalez Bobes, David Marcoux*

引用次数: 13

Abstract

This communication highlights the use of chiral sulfinamides as nitrogen nucleophiles in intermolecular aza-Michael reactions. When chiral sulfinamides are coupled to a chloroethyl group, the corresponding novel annulating reagents can be used to streamline the stereoselective synthesis of complex pyrrolidine-containing molecules. As a result, it has enabled a medicinal chemistry campaign for the synthesis of biologically active RORγt inverse agonists.

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用亚胺环化试剂一步法合成非对映选择性吡咯烷

这篇通讯强调了手性亚胺作为氮亲核试剂在分子间aza-Michael反应中的应用。当手性亚胺与氯乙基偶联时，相应的新型环化试剂可用于简化含吡咯烷络合物分子的立体选择性合成。因此，它使合成具有生物活性的rorγ - t逆激动剂的药物化学运动成为可能。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.