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

Type
Article
Authors
Chatupheeraphat, Adisak
Liao, Hsuan-Hung
Mader, Steffen
Sako, Makoto
Sasai, Hiroaki
Atodiresei, Iuliana
Rueping, Magnus cc
KAUST Department
Chemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2016-03-08
Online Publication Date
2016-03-08
Print Publication Date
2016-04-04
Permanent link to this record
http://hdl.handle.net/10754/623140

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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.
Citation
Chatupheeraphat A, Liao H-H, Mader S, Sako M, Sasai H, et al. (2016) Asymmetric Brønsted Acid Catalyzed Substitution of Diaryl Methanols with Thiols and Alcohols for the Synthesis of Chiral Thioethers and Ethers. Angewandte Chemie International Edition 55: 4803–4807. Available: http://dx.doi.org/10.1002/anie.201511179.
Sponsors
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.
Publisher
Wiley-Blackwell
Journal
Angewandte Chemie International Edition
DOI
10.1002/anie.201511179
10.1002/ange.201511179
Collections
Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)