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Sulfenofunctionalization of Chiral α-Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF3, SCF2R, SCN and SAr Compounds
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0003-4346-8714
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Analytical Chemistry.
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.ORCID iD: 0000-0001-7947-3860
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-9349-7137
2022 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 61, no 46, article id e202210509Article in journal (Refereed) Published
Abstract [en]

We report herein a new method for the synthesis of densely functionalized chiral allyl SCF3, SCF2R, SCN and SAr species with a separate CF3 functionality. The synthetic approach is based on selenium-catalyzed sulfenofunctionalization of chiral α-CF3 allylboronic acids. The reactions proceeded with remarkably high stereo-, diastereo- and site-selectivity, based on the formation of a stable thiiranium ion followed by rapid deborylative ring opening. © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Place, publisher, year, edition, pages
2022. Vol. 61, no 46, article id e202210509
Keywords [en]
Asymmetric Synthesis, Boron, Fluorine, Lewis Base, Sulfur, Synthetic aperture radar, A-stable, Diastereoselectivities, Functionalized, Ring opening, Site selectivity, Synthetic approach, Trifluoromethyl
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-211707DOI: 10.1002/anie.202210509PubMedID: 36152310Scopus ID: 2-s2.0-85139816780OAI: oai:DiVA.org:su-211707DiVA, id: diva2:1713555
Note

Export Date: 22 November 2022; Article; CODEN: ACIEF; Correspondence Address: Szabó, K.J.; Department of Organic Chemistry, Sweden; email: kalman.j.szabo@su.se

Available from: 2022-11-25 Created: 2022-11-25 Last updated: 2022-11-25Bibliographically approved

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Wang, QiangNilsson, TomasEriksson, LarsSzabó, Kálmán J.

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