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无酸、氨基硼烷介导的Ugi型反应,可实现仲胺的广泛应用。

Acid-free, aminoborane-mediated Ugi-type reaction leading to general utilization of secondary amines.

作者信息

Tanaka Yusuke, Hasui Tomoaki, Suginome Michinori

机构信息

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.

出版信息

Org Lett. 2007 Oct 25;9(22):4407-10. doi: 10.1021/ol701570c. Epub 2007 Sep 22.

Abstract

A variety of secondary amines have become utilized in the Ugi reaction by using aminoborane 1 as an iminium ion generator. Aldehydes, secondary amines, and isocyanides are coupled in the presence of 1 at room temperature, giving the corresponding alpha-amino amides in good yields. The nonacidic reaction conditions are beneficial for unique chemoselectivity, where the aldimine functionality is left intact in the present Ugi-type reaction.

摘要

通过使用氨基硼烷1作为亚胺离子生成剂,多种仲胺已被用于乌吉反应。在1存在的情况下,醛、仲胺和异腈在室温下偶联,以良好的产率得到相应的α-氨基酰胺。非酸性反应条件有利于独特的化学选择性,在目前的乌吉型反应中,醛亚胺官能团保持完整。

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