Asymmetric Brønsted Acid Catalyzed Substitution of Diaryl Methanols with Thiols and Alcohols for the Synthesis of Chiral Thioethers and Ethers

Adisak Chatupheeraphat, Hsuan-Hung Liao, Steffen Mader, Makoto Sako, Hiroaki Sasai, Iuliana Atodiresei, Magnus Rueping

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Abstract

An enantioselective addition of thiols and alcohols to aza-ortho-quinone methides, starting from diaryl methanols, was developed. The asymmetric additions occur under mild reaction conditions in the presence of chiral phosphoric acids and furnish the corresponding adducts with excellent yields and enantioselectivities.
Original languageEnglish (US)
Pages (from-to)4803-4807
Number of pages5
JournalAngewandte Chemie International Edition
Volume55
Issue number15
DOIs
StatePublished - Mar 8 2016

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: S.M. thanks the DFG (Deutsche Forschungsgemeinschaft) for financial support through the International Research Training Group SeleCa (IRTG 1628), H.-H.L. thanks the DAAD for a doctoral fellowship, M.S. thanks the JSPS (Japanese Society for the Promotion of Science) for financial support through the Japanese-German Graduate Externship.

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