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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Diels–Alder Reactions of Chiral Sulfinylquinones: From Sterically Directed to CH–π Directed Stereoselectivity

Ka Ho Chow A , Lawrence R. Gahan A and Elizabeth H. Krenske https://orcid.org/0000-0003-1911-0501 A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Biosciences, The University of Queensland, St Lucia, Qld 4072, Australia.

B Corresponding author. Email: e.krenske@uq.edu.au

Australian Journal of Chemistry 73(10) 934-941 https://doi.org/10.1071/CH19525
Submitted: 17 October 2019  Accepted: 25 November 2019   Published: 1 April 2020

Abstract

Density functional theory calculations were performed to determine the origins of chemoselectivity and the mechanisms of stereoinduction in sulfinylquinone Diels–Alder reactions. Computations with M06-2X-D3//B3LYP-D3 indicate that a CH–π interaction between the diene and a chiral p-tolylsulfinyl group attached to the quinone can favour addition to the more crowded diastereotopic face of the remote C=C bond. The effects of a ZnBr2 catalyst and of different sulfinyl substituents on the outcomes of sulfinylquinone Diels–Alder reactions are explored.


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