Sulfenofunctionalization of Chiral α-Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF3, SCF2R, SCN and SAr Compounds
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.202210509ISI: 000868746900001PubMedID: 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
2022-11-252022-11-252024-05-24Bibliographically approved