Synlett 2017; 28(20): 2777-2782
DOI: 10.1055/s-0036-1588583
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© Georg Thieme Verlag Stuttgart · New York

Radical Stabilization Algorithm as a Predictive Tool for Novel and Reported Noncanonical Thiele’s Acid Analogues

Jun Chen
Department of Chemistry, University of Victoria, Victoria, BC, V8W 3V6, Canada   eMail: wulff@uvic.ca
,
Lingxiao Lu
Department of Chemistry, University of Victoria, Victoria, BC, V8W 3V6, Canada   eMail: wulff@uvic.ca
,
Jeremy E. Wulff*
Department of Chemistry, University of Victoria, Victoria, BC, V8W 3V6, Canada   eMail: wulff@uvic.ca
› Institutsangaben

This work was supported by the National Science and Engineering ­Research Council of Canada (NSERC), and by the Michael Smith Foundation for Health Research.
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Publikationsverlauf

Received: 25. Juli 2017

Accepted after revision: 08. September 2017

Publikationsdatum:
06. Oktober 2017 (online)


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This paper is dedicated to Professor Victor Snieckus, in honour of his 80th birthday

Abstract

We recently showed that a simple radical-stabilization algorithm outperformed traditional frontier-molecular orbital methods for rationalizing the outcome of the venerable Thiele’s acid (or ester) Diels–Alder dimerization. In the present Communication, we describe a novel noncanonical Thiele-type dimerization of a cyclopentadiene phosphine oxide, and show that when steric factors are taken into account the ­radical-stabilization method once again correctly rationalizes the regio­chemical outcome for the reaction. We further show that the method appears to be general for all known Thiele- and half-Thiele dimerization events.

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