Author:
Briggs Edward L.,Ma Tsz‐Kan,Zhong Zhenhao,Tota Arianna,Degennaro Leonardo,Luisi* Renzo,Bull* James A.
Abstract
Abstract
This chapter presents the procedure for synthesis of enantioenriched NH‐sulfoximines by NH transfer to sulfoxides using ammonium carbamate and (diacetoxyiodo) benzene. Sulfoximines are emerging motifs in the life sciences and have shown application in asymmetric synthesis as chiral auxiliaries, ligands and catalysts. Their Lewis basic character has also made them interesting directing groups for C‐H functionalization. In 2016, the authors reported an operationally simple, metal‐free protocol for the preparation of NH‐sulfoximines from sulfoxides, using ammonium carbamate as a convenient source of ammonia and (diacetoxyiodo) benzene as the oxidant. They (and others) later reported the synthesis of NH‐sulfoximines directly from sulfides under similar conditions, as well as the synthesis of sulfonimidamides. Overall, the authors expect this metal‐free protocol from enantioenriched sulfoxides to be broad applicable, with the demonstrated compound presenting an attractive building block for further derivatization.
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1. E‐mail: j.bull@imperial.ac.uk orcid: 0000‐0003‐3993‐5818 Department of Chemistry Imperial College London Molecular Sciences Research Hub White City Campus Wood Lane London W12 0BZ UK. Email: renzo.luisi@uniba.it orcid: 0000‐0002‐9882‐7908 Department of Pharmacy‐Drug Sciences University of Bari “A. Moro” Via E. Orabona 4 Bari 70125 Italy. We gratefully acknowledge The Royal Society [University Research Fellowship UF140161 and URF\R\201019 (to J.A.B.) URF appointed grant RG150444 and URF enhancement grant RGF\EA\180031] and EPSRC [Impact Acceleration Account (EP/K503733/1) DTA Studentship (to E.L.B.)]. This research was supported by the project MISE Horizon 2020 – PON 2014/2020 FARMIDIAB “code 338” the University of Bari.
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