Bicyclo[1.1.1]pentyl Sulfoximines : Synthesis and Functionalizations

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dc.contributor University of Helsinki, Department of Chemistry en
dc.contributor.author Bär, Robin M.
dc.contributor.author Langer, Lukas
dc.contributor.author Nieger, Martin
dc.contributor.author Bräse, Stefan
dc.date.accessioned 2020-05-12T11:52:01Z
dc.date.available 2020-05-12T11:52:01Z
dc.date.issued 2020-03-17
dc.identifier.citation Bär , R M , Langer , L , Nieger , M & Bräse , S 2020 , ' Bicyclo[1.1.1]pentyl Sulfoximines : Synthesis and Functionalizations ' , Advanced Synthesis & Catalysis , vol. 362 , no. 6 , pp. 1356-1361 . https://doi.org/10.1002/adsc.201901453 en
dc.identifier.issn 1615-4150
dc.identifier.other PURE: 132589975
dc.identifier.other PURE UUID: f7c31035-27b4-4398-af97-fa8239062e46
dc.identifier.other RIS: urn:7255C47977C2240220A7E8F2E8771ED2
dc.identifier.other WOS: 000512817600001
dc.identifier.other ORCID: /0000-0003-1677-0109/work/74065990
dc.identifier.uri http://hdl.handle.net/10138/314787
dc.description.abstract 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. en
dc.format.extent 6
dc.language.iso eng
dc.relation.ispartof Advanced Synthesis & Catalysis
dc.rights en
dc.subject bicyclo[1.1.1]pentane en
dc.subject bioisostere en
dc.subject sulfoximine en
dc.subject copper en
dc.subject arylation en
dc.subject 116 Chemical sciences en
dc.title Bicyclo[1.1.1]pentyl Sulfoximines : Synthesis and Functionalizations en
dc.type Article
dc.description.version Peer reviewed
dc.identifier.doi https://doi.org/10.1002/adsc.201901453
dc.type.uri info:eu-repo/semantics/other
dc.type.uri info:eu-repo/semantics/publishedVersion
dc.contributor.pbl

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