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
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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