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Studies of stereo-selective cyclo-additions and transformations of substituted 2-cyclopenten-1-one with chiral anthracene templates

Phutdhawong, Weerachai; Eksinitkun, Gedsirin; Jaroensuk, Yonlada; Willis, Anthony; Phutdhawong, Waya S.


The chiral (S)-9-(1-methoxyethyl), (R)-9-(1,2-dimethoxyethyl) and 9-(1R, 2R)-(1,2-dimethoxypropyl) anthracenes were synthesised and used for the thermal Diels-Alder reaction with cyclopentene-3,5-dione. Unlike the maleic anhydride and N-substituted malemides, the cyclo-adducts were obtained with high regio-selectivity as a single diastereomer. The X-ray structure of the cyclo-adduct showed an enol form but the 13C NMR showed resonances for two cyclopentanone carbonyl groups suggesting the...[Show more]

CollectionsANU Research Publications
Date published: 2017
Type: Journal article
Source: Oriental Journal of Chemistry
DOI: 10.13005/ojc/330601
Access Rights: Open Access


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