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Issue 44, 2019
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Catalytic, transannular carbonyl-olefin metathesis reactions

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Abstract

Transannular carbonyl–olefin metathesis reactions complement existing procedures for related ring-closing, ring-opening, and intermolecular carbonyl-olefin metathesis. We herein report the development and mechanistic investigation of FeCl3-catalyzed transannular carbonyl-olefin metathesis reactions that proceed via a distinct reaction path compared to previously reported ring-closing and ring-opening protocols. Specifically, carbonyl-ene and carbonyl-olefin metathesis reaction pathways are competing under FeCl3-catalysis to ultimately favor metathesis as the thermodynamic product. Importantly, we show that distinct Lewis acid catalysts are able to distinguish between these pathways to enable the selective formation of either transannular carbonyl-ene or carbonyl-olefin metathesis products. These insights are expected to enable further advances in catalyst design to efficiently differentiate between these two competing reaction paths of carbonyl and olefin functionalities to further expand the synthetic generality of carbonyl-olefin metathesis.

Graphical abstract: Catalytic, transannular carbonyl-olefin metathesis reactions

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Supplementary files

Article information


Submitted
28 Jul 2019
Accepted
19 Sep 2019
First published
25 Sep 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 10267-10274
Article type
Edge Article

Catalytic, transannular carbonyl-olefin metathesis reactions

P. S. Riehl, D. J. Nasrallah and C. S. Schindler, Chem. Sci., 2019, 10, 10267
DOI: 10.1039/C9SC03716K

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