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Diastereomeric control of photoinduced Diels-Alder reactions of 1-anthracen-9-yl-ethanol by hydrogen-bonding effects

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

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Abstract

Photoinduced Diels-Alder reactions of 1-anthracen-9-yl-ethanol with maleic anhydride proceed with high diastereoselection but with complete reversal of the sense of selectivity compared to analogous O-methyl compound. Hydrogen-bonding effects have been established as the predominant factors in determining this selectivity. © 2001 Elsevier Science Ltd. All rights reserved.

Publication metadata

Author(s): Atherton JCC, Jones S

Publication type: Article

Publication status: Published

Journal: Tetrahedron Letters

Year: 2001

Volume: 42

Issue: 46

Pages: 8239-8241

ISSN (print): 0040-4039

ISSN (electronic): 1873-3581

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/S0040-4039(01)01742-7

DOI: 10.1016/S0040-4039(01)01742-7

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