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Issue 18, 2019
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A rhodium catalyzed cycloisomerization and tandem Diels–Alder reaction for facile access to diverse bicyclic and tricyclic heterocycles

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Abstract

A regioselective distal cycloisomerization of 1,6-allenenes was successfully developed to afford six-membered ring exocyclic 1,3-dienes employing a rhodium/diphosphine catalyst system. Deuterium labelling experiments and DFT calculations were performed to provide insights into the reaction mechanism of this unprecedented transformation. In addition, one-pot tandem Diels–Alder reactions with various dienophiles could readily construct diverse bicyclic and tricyclic nitrogen heterocycles, which are ubiquitous core scaffolds for a variety of natural products and bioactives. High efficiency and exclusive chemo and regioselectivities for a broad substrate scope were achieved under mild conditions using a low catalyst loading of 0.5 mol%.

Graphical abstract: A rhodium catalyzed cycloisomerization and tandem Diels–Alder reaction for facile access to diverse bicyclic and tricyclic heterocycles

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Article information


Submitted
26 Feb 2019
Accepted
01 Apr 2019
First published
03 Apr 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, 4805-4810
Article type
Edge Article

A rhodium catalyzed cycloisomerization and tandem Diels–Alder reaction for facile access to diverse bicyclic and tricyclic heterocycles

Y. Zhou, A. Nikbakht, F. Bauer and B. Breit, Chem. Sci., 2019, 10, 4805
DOI: 10.1039/C9SC00980A

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