Issue 33, 2019

Nucleophile-intercepted Beckmann fragmentation reactions

Abstract

We describe the first examples of nucleophile-intercepted Beckmann fragmentations of indoline oximes. This reaction uses MsCl as a promoter to give cyano chlorides and is believed to proceed through an aziridinium intermediate via a double stereoinvertive process. Mechanistic insights have led to the further discovery that oxygen, nitrogen, and bromide nucleophiles can be employed for this fragmentation by the use of other promoters. We envision that these products may be useful in the syntheses of members of the akuammiline and koumine families of indoline alkaloids.

Graphical abstract: Nucleophile-intercepted Beckmann fragmentation reactions

Supplementary files

Article information

Article type
Edge Article
Submitted
22 Feb 2019
Accepted
22 Jun 2019
First published
04 Jul 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 7812-7815

Nucleophile-intercepted Beckmann fragmentation reactions

S. J. Touchette, E. M. Dunkley, L. L. Lowder and J. Wu, Chem. Sci., 2019, 10, 7812 DOI: 10.1039/C9SC00926D

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