Issue 10, 2017

Remote C–H insertion of vinyl cations leading to cyclopentenones

Abstract

We report a Lewis acid catalyzed reaction sequence involving a 1,2-shift and subsequent C–H insertion that gives monocyclic and fused bicyclic cyclopentenone products. This reaction sequence, which is initiated by treating β-hydroxy-α-diazo ketones with a Lewis acid, proceeds through vinyl cation intermediates that insert at non-activated gamma C–H bonds. This reaction represents an alternative strategy to exploit the diazo functional group in an intramolecular C–H insertion, and can provide products not accessible by transition metal catalyzed C–H insertions. This remote C–H activation process provides good yields of bicyclic cyclopentenone products that contain 7- and 8-membered rings, and monocyclic prostaglandin analogs.

Graphical abstract: Remote C–H insertion of vinyl cations leading to cyclopentenones

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Jun 2017
Accepted
20 Jul 2017
First published
03 Aug 2017
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., 2017,8, 6810-6814

Remote C–H insertion of vinyl cations leading to cyclopentenones

S. E. Cleary, M. J. Hensinger and M. Brewer, Chem. Sci., 2017, 8, 6810 DOI: 10.1039/C7SC02768K

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