Literature DB >> 17217303

A convenient, NMR-based method for the analysis of diastereomeric mixtures of pseudoephedrine amides.

William J Chain1, Andrew G Myers.   

Abstract

Amides of pseudoephedrine and ephedrine are shown to undergo highly stereospecific, invertive cyclization to form 4,5-dihydro-3,4-dimethyl-5-phenyl-1,3-oxazolium triflate derivatives in the presence of triflic anhydride-pyridine. 1H NMR spectra of the unpurified reaction products are remarkably clean, with sharp, well-defined peaks, and allow for rapid assessment of the diastereomeric purities of the starting amides. [reaction: see text].

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Year:  2007        PMID: 17217303     DOI: 10.1021/ol0628762

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


  4 in total

1.  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides.

Authors:  Gary A Molander; Inji Shin; Ludivine Jean-Gérard
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

2.  Pseudoephenamine: a practical chiral auxiliary for asymmetric synthesis.

Authors:  Marvin R Morales; Kevin T Mellem; Andrew G Myers
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-27       Impact factor: 15.336

3.  A concise and versatile double-cyclization strategy for the highly stereoselective synthesis and arylative dimerization of Aspidosperma alkaloids.

Authors:  Jonathan William Medley; Mohammad Movassaghi
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-12       Impact factor: 15.336

4.  Stereocontrolled alkylative construction of quaternary carbon centers.

Authors:  David A Kummer; William J Chain; Marvin R Morales; Olga Quiroga; Andrew G Myers
Journal:  J Am Chem Soc       Date:  2008-09-13       Impact factor: 15.419

  4 in total

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