Studies of stereo-selective cyclo-additions and transformations of substituted 2-cyclopenten-1-one with chiral anthracene templates
Date
2017
Authors
Phutdhawong, Weerachai
Eksinitkun, Gedsirin
Jaroensuk, Yonlada
Willis, Anthony
Phutdhawong, Waya S.
Journal Title
Journal ISSN
Volume Title
Publisher
Oriental Scientific Publishing Company, Inc.
Abstract
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 solution structure is in the diketone form. Stereo-controlled studies using organomagnesium additions to the carbonyl groups resulted in hydrolytic cleavage of the enol ether and elimination of water to give β-alkylketone anthracene adducts. These were unsuccessful in preparing chiral cyclopentenone core structures.
Description
Keywords
Citation
Collections
Source
Oriental Journal of Chemistry
Type
Journal article
Book Title
Entity type
Access Statement
Open Access
License Rights
Attribution-NonCommercial-ShareAlike 3.0 Unported (CC BY-NC-SA 3.0)