Katharina Röser, Lucas Prameshuber, Sajid Jahangir, Sharath Chandra Mallojjala, Jennifer S. Hirschi, Mario Waser
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引用次数: 0
Abstract
We herein report a protocol for the asymmetric 1,4-addition of hydantoins to various Michael acceptors by utilizing Cinchona alkaloid-based chiral quaternary ammonium salt catalysts. Various products were obtained with moderate to good enantioselectivities and accompanying computational investigations helped to identify key interactions responsible for the observed selectivity. DFT calculations along with non-covalent interaction plots reveal the presence of numerous stabilizing non-classical hydrogen bonding interactions along with other non-covalent interactions between the chiral quaternary ammonium salt and hydantoin molecule in the C−C bond forming transition states leading to the formation of the products. In addition, a first proof-of-concept for an analogous a-sulfanylation reaction, albeit with poor selectivity, is reported as well.
期刊介绍：
Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance.
Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.
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