Literature DB >> 23149421

Highly cis-selective synthesis of iodo-aziridines using diiodomethyllithium and in situ generated N-Boc-imines.

James A Bull1, Tom Boultwood, Thomas A Taylor.   

Abstract

The first preparation of iodoaziridines is described. The addition of diiodomethyllithium to N-Boc-imines affords these novel aziridines in high yields. The reaction proceeds in one-pot via a highly diastereoselective cyclisation of an amino gem-diiodide intermediate.

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Year:  2012        PMID： 23149421     DOI： 10.1039/c2cc37029h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  5 in total

Review 1.  Transition metal-free one-pot synthesis of nitrogen-containing heterocycles.

Authors:  Simpal Kumari; Dharma Kishore; Sarvesh Paliwal; Rajani Chauhan; Jaya Dwivedi; Aakanksha Mishra
Journal:  Mol Divers       Date:  2015-06-09       Impact factor: 2.943

2.  Elucidation of the Reaction Mechanism of C2 + N1 Aziridination from Tetracarbene Iron Catalysts.

Authors:  Sara B Isbill; Preeti P Chandrachud; Jesse L Kern; David M Jenkins; Sharani Roy
Journal:  ACS Catal       Date:  2019-05-31       Impact factor: 13.084

3.  Synthesis and purification of iodoaziridines involving quantitative selection of the optimal stationary phase for chromatography.

Authors:  Tom Boultwood; Dominic P Affron; James A Bull
Journal:  J Vis Exp       Date:  2014-05-16       Impact factor: 1.355

4.  Telescoped, Divergent, Chemoselective C1 and C1-C1 Homologation of Imine Surrogates: Access to Quaternary Chloro- and Halomethyl-Trifluoromethyl Aziridines.

Authors:  Laura Ielo; Saad Touqeer; Alexander Roller; Thierry Langer; Wolfgang Holzer; Vittorio Pace
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-24       Impact factor: 15.336

5.  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
  5 in total

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