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Mechanistic investigations in diastereoselective Diels-Alder additions of chiral 9-anthrylethanol derivatives

Lookup NU author(s): Jonathan Atherton, Dr Simon Jones

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Abstract

The preparation and subsequent Diels-Alder addition reactions of chiral 9-functionalised anthracene derivatives have been investigated. 9-(1-Methoxyethyl) anthracene undergoes highly diastereoselective (> 95 : 5) thermal and photoinduced Diels-Alder additions with maleic anhydride and N-methylmaleimide. The corresponding reactions of 1-anthracen-9-ylethanol occur with the reverse sense of selectivity for additions with maleic anhydride with a corresponding increase in the reaction rate. The origins of this selectivity have been proposed to lie in hydrogen-bonding effects. The stereochemical outcome of the Diels-Alder additions has been determined from single X-ray crystallography of adducts 5 and 7. Solvent effects on the diastereoselectivity of these reactions have also been observed.

Publication metadata

Author(s): Atherton JCC, Jones S

Publication type: Article

Publication status: Published

Journal: Journal of the Royal Chemical Society: Perkin Transactions 1

Year: 2002

Issue: 19

Pages: 2166-2173

ISSN (print): 1472-7781

ISSN (electronic): 1364-5463

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b206523a

DOI: 10.1039/b206523a

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