A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes

Emily Kiss; Craig D. Campbell; Russell W. Driver; John D. Jolliffe; Rosemary Lang; Tetiana Sergeieva; Sergiy Okovytyy; Robert S. Paton; Martin D. Smith

doi:10.1002/anie.201608534

A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes

Emily Kiss
, Craig D. Campbell
, Russell W. Driver
, John D. Jolliffe
, Rosemary Lang
, Tetiana Sergeieva
, Sergiy Okovytyy
, Robert S. Paton
, Martin D. Smith

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

An approach to the intramolecular Diels–Alder reaction has led to a cascade synthesis of complex carbocycles composed of three fused rings and up to five stereocenters with complete stereocontrol. Computational analysis reveals that the reaction proceeds by a Michael/Michael/cyclopropanation/epimerization cascade in which size and coordination of the counterion is key.

Original language	English
Pages (from-to)	13813-13817
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	55
Issue number	44
DOIs	https://doi.org/10.1002/anie.201608534
State	Published - Oct 24 2016

Funding

The European Research Council has provided financial support (FP7/2007-2013)/ ERC grant agreement no. 259056. We gratefully acknowledge the Diamond Light Source for an award of instrument time on I19 (MT7768). This work was supported by EPSRC (EP/I003398/1 and EP/K014668/1). We acknowledge the Discovery Environment (XSEDE) supported by National Science Foundation grant number OCI-1053575 in carrying out this work.

Keywords

Cations
Cycloadditions
Density-functional calculations
Diastereoselectivity
Heterocycles

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A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes

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