Literature DB >> 15760162

Substituted aziridines by lithiation-electrophile trapping of terminal aziridines.

David M Hodgson1, Philip G Humphreys, John G Ward.   

Abstract

[reaction: see text] Regio- and stereoselective deprotonation of N-Bus (Bus = tert-butylsulfonyl)-protected terminal aziridines with lithium 2,2,6,6-tetramethylpiperidide generates a nonstabilized (H-substituted) aziridinyl anion that undergoes in situ or external electrophile trapping under experimentally straightforward conditions to give trans-disubstituted aziridines in good to excellent yields.

Entities:  

Year:  2005        PMID: 15760162     DOI: 10.1021/ol050060f

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Metalated aziridines for cross-coupling with aryl and alkenyl halides via palladium catalysis.

Authors:  John M Nelson; Edwin Vedejs
Journal:  Org Lett       Date:  2010-10-14       Impact factor: 6.005

2.  α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines.

Authors:  David M Hodgson; Zhaoqing Xu
Journal:  Beilstein J Org Chem       Date:  2010-10-13       Impact factor: 2.883

3.  Synthesis of cis-C-iodo-N-tosyl-aziridines using diiodomethyllithium: reaction optimization, product scope and stability, and a protocol for selection of stationary phase for chromatography.

Authors:  Tom Boultwood; Dominic P Affron; Aaron D Trowbridge; James A Bull
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

  3 in total

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