Literature DB >> 26952288

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

Adisak Chatupheeraphat1, Hsuan-Hung Liao1, Steffen Mader1, Makoto Sako2, Hiroaki Sasai2, Iuliana Atodiresei1, Magnus Rueping3,4.   

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.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Brønsted acids; Michael addition; carbenium ions; ortho-quinone methides; substitution

Year:  2016        PMID: 26952288     DOI: 10.1002/anie.201511179

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  3 in total

1.  Asymmetric Organocatalytic Sulfa-Michael Addition to Enone Diesters.

Authors:  Jennifer L Fulton; Matthew A Horwitz; Ericka L Bruske; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2018-03-07       Impact factor: 4.354

2.  Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes - a reaction at the 'oxonium-Prins' vs. 'ortho-quinone methide cycloaddition' mechanistic nexus.

Authors:  Christian D-T Nielsen; Wouter J Mooij; David Sale; Henry S Rzepa; Jordi Burés; Alan C Spivey
Journal:  Chem Sci       Date:  2018-10-19       Impact factor: 9.825

3.  Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst-Controlled Cyclization of ortho-Quinone Methide Iminiums.

Authors:  Xingxing Wu; Christof Sparr
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-25       Impact factor: 16.823

  3 in total

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