Origin of diastereoselectivity and catalytic efficiency on Isothiourea-mediated cyclization of carboxylic acid with alkenyl ketone
COMPUTATIONAL AND THEORETICAL CHEMISTRY(2020)
摘要
Asymmetric synthesis plays an important role in organic chemistry. To this end, a theoretical study of the possible mechanisms, origin of diastereoselectivity, and efficiency of catalysts on isothiourea-catalyzed asymmetric cyclization of carboxylic acids and alkenyl ketones was performed by using density functional theory (DFT). The calculated results show that the diastereoselectivity can be induced in the C-C bond formation step involved in the [4 + 2] cycloaddition. The atoms-in-molecules (AIM) analysis shows that bonding interaction and hydrogen bonds contribute significantly for the favorability of SS-configured product. The catalytic efficiency of isothioureas was explored and predicted by nucleophilic atom energy E-a(-).
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关键词
Diastereoselectivity,Cyclization,Density functional theory (DFT),Reaction mechanism
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