Literature DB >> 19938003

Synthesis of enantiopure sulfonimidamides and elucidation of their absolute configuration by comparison of measured and calculated CD spectra and X-ray crystal structure determination.

Christin Worch1, Iuliana Atodiresei, Gerhard Raabe, Carsten Bolm.   

Abstract

Straightforward syntheses of enantiopure N-benzoyl- and N-tert-butyloxycarbonyl-protected sulfonimidamides, which can be used as building blocks in newly designed catalysts, are presented. Key synthetic step is a dynamic resolution of a racemic sulfinic acid sodium salt. All subsequent transformations proceed stereospecifically. The absolute configurations at the sulfur atoms of both sulfonimidamides were determined by comparison of measured and calculated CD spectra. An X-ray crystal structure determination of a sulfonimidoylguanidine derivative confirmed this result.

Entities:  

Year:  2010        PMID: 19938003     DOI: 10.1002/chem.200901715

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  6 in total

1.  Synthesis and functionalization of cyclic sulfonimidamides: a novel chiral heterocyclic carboxylic Acid bioisostere.

Authors:  Nils Pemberton; Henrik Graden; Emma Evertsson; Emma Bratt; Matti Lepistö; Petra Johannesson; Per H Svensson
Journal:  ACS Med Chem Lett       Date:  2012-05-30       Impact factor: 4.345

2.  Exploiting Configurational Lability in Aza-Sulfur Compounds for the Organocatalytic Enantioselective Synthesis of Sulfonimidamides.

Authors:  Michael J Tilby; Damien F Dewez; Adrian Hall; Carolina Martínez Lamenca; Michael C Willis
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-02       Impact factor: 16.823

3.  N-Trifluoromethylthiolated Sulfonimidamides and Sulfoximines: Anti-microbial, Anti-mycobacterial, and Cytotoxic Activity.

Authors:  Niranjan Thota; Parameshwar Makam; Kamal K Rajbongshi; Savania Nagiah; Naeem Sheik Abdul; Anil A Chuturgoon; Amit Kaushik; Gyanu Lamichhane; Anou M Somboro; Hendrik G Kruger; Thavendran Govender; Tricia Naicker; Per I Arvidsson
Journal:  ACS Med Chem Lett       Date:  2019-09-11       Impact factor: 4.345

4.  Additions to N-Sulfinylamines as an Approach for the Metal-free Synthesis of Sulfonimidamides: O-Benzotriazolyl Sulfonimidates as Activated Intermediates.

Authors:  Maximilian Bremerich; Christian M Conrads; Tim Langletz; Carsten Bolm
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-11       Impact factor: 15.336

5.  Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds.

Authors:  Elżbieta Wojaczyńska; Jacek Wojaczyński
Journal:  Chem Rev       Date:  2020-04-29       Impact factor: 60.622

6.  Silicon-Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism.

Authors:  Dong-Dong Liang; Dieuwertje E Streefkerk; Daan Jordaan; Jorden Wagemakers; Jacob Baggerman; Han Zuilhof
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-11       Impact factor: 15.336

  6 in total

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