Abstract
In our recent studies, we have investigated the photocatalytic ring opening of various α-epoxyketones of interest by TPT as photocatalyst in the presence of methanol [7], cyclohexanone [8], acetic acid [9], and acetone [10]. The aims of these studies were to elucidate the effect of the additional substituent on the parent molecule and the nucleophilicity and also the steric hindranceof the solventmoleculeon the rate and diastereoselectivity of the reaction. Among the nucleophiles studied, only the reaction in the presenceof cyclohexanone resulted in the formation of a single diastereomer. The reason is possibly the steric hindrance of cyclohexanone compared to other nucleophiles in the attack on the proposed reaction intermediates from theless hinderedside [8].In continuationof thesestudies, we have investigated the photocatalytic ring opening of certain α-epoxyketones by TPT in cyclopentanone to elucidate the effect of the nature and the steric hindrance of the nucleophile on the diastereoselectivity of the reaction.
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