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

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 e...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-04, Vol.55 (15), p.4803-4807
Main Authors: Chatupheeraphat, Adisak, Liao, Hsuan-Hung, Mader, Steffen, Sako, Makoto, Sasai, Hiroaki, Atodiresei, Iuliana, Rueping, Magnus
Format: Article
Language:English
Subjects:
Acids
Adducts
Alcohol
Alcohols
Asymmetry
Brønsted acids
carbenium ions
Enantiomers
Ethers
Michael addition
ortho-quinone methides
Quinones
substitution
Thioethers
Thiols
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Summary: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. Take two: An enantioselective addition of thiols and alcohols to aza‐ortho‐quinone methides, starting from diaryl methanols, has been developed. The asymmetric oxa‐ and sulfa‐Michael additions proceed under mild reaction conditions in the presence of chiral phosphoric acids to furnish the corresponding adducts with excellent yields and enantioselectivities.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201511179