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Bicyclo[1.1.1]pentyl Sulfoximines: Synthesis and Functionalizations

Bär, Robin M.; Langer, Lukas; Nieger, Martin; Bräse, Stefan

Abstract:
Herein we present the first synthesis of bicyclo[1.1.1]pentyl (BCP) sulfoximines from the corresponding sulfides. Both BCPs and sulfoximines are bioisosteres used in medicinal chemistry and therefore desirable motifs. The access to BCP sulfides was enabled by the thiol addition to [1.1.1]propellane as published before. A broad scope with specific limitations was discovered for the sulfoximination. To diversify the sulfoximines, N-acylations and N-arylations were performed. As the N-arylation was low yielding we optimized the copper(I) catalyzed reaction. A wide range of aryl iodides could be deployed and competitive reactions showed that aryl bromides react equally fast. In a scale-up we prepared a suitable precursor for a BCP drug analogue.
In this work several molecular structures could be determined by single-crystal X-ray diffraction.


Verlagsausgabe §
DOI: 10.5445/IR/1000117419
Veröffentlicht am 26.02.2020
Originalveröffentlichung
DOI: 10.1002/adsc.201901453
Scopus
Zitationen: 4
Dimensions
Zitationen: 3
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 17.03.2020
Sprache Englisch
Identifikator ISSN: 1615-4150, 1615-4169
KITopen-ID: 1000117419
HGF-Programm 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in Advanced synthesis & catalysis
Verlag John Wiley and Sons
Band 362
Heft 6
Seiten 1356-1361
Vorab online veröffentlicht am 03.02.2020
Schlagwörter bicyclo[1.1.1]pentane, bioisostere, sulfoximine, copper, arylation
Nachgewiesen in Dimensions
Web of Science
Scopus
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