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Issue 38, 2019
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Origins of stereoselectivity in uncatalyzed and ZnBr2-catalyzed Diels–Alder reactions of a chiral sulfinylquinone

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Abstract

Density functional theory calculations are reported which explore how a chiral sulfinyl substituent controls the stereoselectivities of the Diels–Alder reactions of a 2-p-tolylsulfinylbenzoquinone. The π-facial stereoselectivities vary depending on the diene (cyclopentadiene or trans-piperylene) and on the presence or absence of a ZnBr2 catalyst. The stereoselectivities are shown to be controlled by steric effects and non-covalent (CH–π) interactions. The calculations reveal that the active dienophile in the ZnBr2-catalyzed reactions is likely to be a 1 : 2 complex of the dienophile and catalyst, not a 1 : 1 complex as commonly assumed.

Graphical abstract: Origins of stereoselectivity in uncatalyzed and ZnBr2-catalyzed Diels–Alder reactions of a chiral sulfinylquinone

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Publication details

The article was received on 09 Aug 2019, accepted on 11 Sep 2019 and first published on 25 Sep 2019


Article type: Paper
DOI: 10.1039/C9OB01756A
Org. Biomol. Chem., 2019,17, 8756-8767

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    Origins of stereoselectivity in uncatalyzed and ZnBr2-catalyzed Diels–Alder reactions of a chiral sulfinylquinone

    K. H. Chow and E. H. Krenske, Org. Biomol. Chem., 2019, 17, 8756
    DOI: 10.1039/C9OB01756A

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