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Sodium Bicyclo[1.1.1]pentanesulfinate: A Bench‐Stable Precursor for Bicyclo[1.1.1]pentylsulfones and Bicyclo‐ [1.1.1]pentanesulfonamides

Bär, Robin M.; Gross, Patrick J.; Nieger, Martin; Bräse, Stefan

Abstract:
Herein, we present the synthesis of the benchstable sodium bicyclo[1.1.1]pentanesulfinate (BCP-SO$_{2}$Na) and its application in the synthesis of bicyclo[1.1.1]pentyl (BCP) sulfones and sulfonamides. The salt can be obtained in a four-step procedure from commercially available precursors in multigram scale without the need for column chromatography or crystallization. Sulfinates are known to be useful precursors in radical and nucleophilic reactions and are widely used in medicinal chemistry. This building block enables access to BCP sulfones and sulfonamides avoiding the volatile [1.1.1]propellane which is favorable for the extension of SAR studies. Further, BCP-SO$_{2}$Na enables the synthesis of products that were not available with previous methods. A chlorination of BCP-SO$_{2}$Na and subsequent reaction with a Grignard reagent provides a new route to BCP sulfoxides. Several products were analyzed by single-crystal X-ray diffraction.


Verlagsausgabe §
DOI: 10.5445/IR/1000117879
Veröffentlicht am 25.03.2020
Originalveröffentlichung
DOI: 10.1002/chem.202000097
Scopus
Zitationen: 6
Dimensions
Zitationen: 5
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 01.04.2020
Sprache Englisch
Identifikator ISSN: 0947-6539, 1521-3765
KITopen-ID: 1000117879
HGF-Programm 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in Chemistry - a European journal
Verlag John Wiley and Sons
Band 26
Heft 19
Seiten 4242-4245
Vorab online veröffentlicht am 10.01.2020
Nachgewiesen in Web of Science
Scopus
Dimensions
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