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不对称 Ugi 3CR 在色胺衍生的亚胺上的反应:手性 3,3-二取代 3-氨基氧吲哚衍生物的合成。

Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives.

机构信息

Dipartimento di Chimica, Università degli Studi di Milano, via C. Golgi, 19, 20133 Milano (Italy).

Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via L. Mangiagalli 25, 20133 Milano, Italy.

出版信息

Beilstein J Org Chem. 2014 Jun 18;10:1383-9. doi: 10.3762/bjoc.10.141. eCollection 2014.

Abstract

An efficient Ugi three-component reaction of a preformed chiral ketimine derived from isatin with various isonitrile and acid components has been developed. The reactions proceeded smoothly and in a stereocontrolled manner with regard to the new center of the Ugi products due to the stereoinduction of the amine chiral residue. A wide variety of novel chiral 3,3-disubstituted 3-aminooxindoles were obtained, a selection of which were subjected to post-Ugi transformations, paving the way to application as peptidomimetics.

摘要

已开发出一种有效的 Ugi 三组分反应,其中前手性酮亚胺是由靛红与各种异腈和酸组分衍生而来。由于胺手性残基的立体诱导作用,反应对于 Ugi 产物的新中心进行了立体控制,反应顺利进行。获得了广泛的新型手性 3,3-二取代 3-氨基氧吲哚,其中一些经过 Ugi 后转化,为用作肽模拟物铺平了道路。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/385f/4077467/3a4d44509a23/Beilstein_J_Org_Chem-10-1383-g002.jpg

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