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

doi:10.1002/anie.201511179

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 language	English (US)
Pages (from-to)	4803-4807
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	55
Issue number	15
DOIs	https://doi.org/10.1002/anie.201511179 https://doi.org/10.1002/ange.201511179
State	Published - 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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Chatupheeraphat, A., Liao, H.-H., Mader, S., Sako, M., Sasai, H., Atodiresei, I., & Rueping, M. (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(15), 4803-4807. https://doi.org/10.1002/anie.201511179, https://doi.org/10.1002/ange.201511179

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title = "Asymmetric Br{\o}nsted Acid Catalyzed Substitution of Diaryl Methanols with Thiols and Alcohols for the Synthesis of Chiral Thioethers and Ethers",

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.",

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

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.",

year = "2016",

month = mar,

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doi = "10.1002/anie.201511179",

language = "English (US)",

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Chatupheeraphat, A, Liao, H-H, Mader, S, Sako, M, Sasai, H, Atodiresei, I & Rueping, M 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, vol. 55, no. 15, pp. 4803-4807. https://doi.org/10.1002/anie.201511179, https://doi.org/10.1002/ange.201511179

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T1 - Asymmetric Brønsted Acid Catalyzed Substitution of Diaryl Methanols with Thiols and Alcohols for the Synthesis of Chiral Thioethers and Ethers

AU - Chatupheeraphat, Adisak

AU - Liao, Hsuan-Hung

AU - Mader, Steffen

AU - Sako, Makoto

AU - Sasai, Hiroaki

AU - Atodiresei, Iuliana

AU - Rueping, Magnus

N1 - 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.

PY - 2016/3/8

Y1 - 2016/3/8

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/623140

UR - http://doi.wiley.com/10.1002/anie.201511179

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DO - 10.1002/anie.201511179

M3 - Article

C2 - 26952288

SN - 1433-7851

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SP - 4803

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JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 15

ER -

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

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