通过偕二酮的形式环加成合成 γ-内酰胺。

Synthesis of γ-Lactams by Formal Cycloadditions with Ketenes.

机构信息

Univ. Grenoble Alpes, CNRS, DCM, 301 rue de la chimie, 38000 Grenoble, France.

出版信息

Org Lett. 2021 Apr 2;23(7):2449-2454. doi: 10.1021/acs.orglett.1c00335. Epub 2021 Mar 11.

DOI:10.1021/acs.orglett.1c00335

Abstract

The synthesis of γ-lactams is reported by a formal (3+2) cycloaddition between readily available ketenes and aziridines or a one-pot formal (2+1+2) cycloaddition using imines as aziridine precursors. The method is practical, is scalable, and affords high yields. It also offers a high level of regio- and diastereoselectivity on a wide range of substrates as well as a high stereoselectivity in the case of enantiopure aziridines.

摘要

γ-内酰胺的合成是通过 readily available ketenes（烯酮）与 aziridines（氮丙啶）之间的（3+2）环加成反应，或者使用 imines（亚胺）作为氮丙啶前体的一锅法（2+1+2）环加成反应来报道的。该方法实用、可扩展，并且产率高。它还在广泛的底物范围内提供了高水平的区域和立体选择性，以及在对映纯氮丙啶的情况下具有高立体选择性。

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