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Organocatalytic Asymmetric Synthesis of 1,1-Diarylethanes by Transfer Hydrogenation

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Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China
Department of Biology and Chemistry, City University of Hong Kong, Kowloon Tong, Hong Kong SAR, China
Cite this: J. Am. Chem. Soc. 2015, 137, 1, 383–389
Publication Date (Web):December 8, 2014
https://doi.org/10.1021/ja510980d
Copyright © 2014 American Chemical Society

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    Abstract

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    A new organocatalytic transfer hydrogenation strategy for the asymmetric synthesis of 1,1-diarylethanes is described. Under mild conditions, a range of 1,1-diarylethanes substituted with an o-hydroxyphenyl or indole unit could be obtained with excellent efficiency and enantioselectivity. We also extended the protocol to an unprecedented asymmetric hydroarylation of 1,1-diarylalkenes with indoles for the synthesis of a range of highly enantioenriched 1,1,1-triarylethanes bearing acyclic all-carbon quaternary stereocenters. These diaryl- and triarylethanes exhibit impressive cytotoxicity against a number of human cancer cell lines. Preliminary mechanistic studies combined with DFT calculations provided important insight into the reaction mechanism.

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