Literature DB >> 17221983

One-pot asymmetric synthesis of either diastereomer of tert-butanesulfinyl-protected amines from ketones.

Jessica Tanuwidjaja1, Hillary M Peltier, Jonathan A Ellman.   

Abstract

A one-pot method for the asymmetric synthesis of tert-butanesulfinyl-protected amines is described. Condensation of aryl alkyl and dialkyl ketones with tert-butanesulfinamide followed by in situ reduction with the appropriate reagent provides either diastereomer of the sulfinamide products in good yields and with diastereomeric ratios of up to 99:1.

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Year:  2007        PMID： 17221983     DOI： 10.1021/jo0616512

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  13 in total

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Journal:  J Org Chem       Date:  2008-05-01       Impact factor: 4.354

4.  Effects of N-Substitutions on the Tetrahydroquinoline (THQ) Core of Mixed-Efficacy μ-Opioid Receptor (MOR)/δ-Opioid Receptor (DOR) Ligands.

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Journal:  Eur J Med Chem       Date:  2018-09-18       Impact factor: 6.514

6.  Further Optimization and Evaluation of Bioavailable, Mixed-Efficacy μ-Opioid Receptor (MOR) Agonists/δ-Opioid Receptor (DOR) Antagonists: Balancing MOR and DOR Affinities.

Authors:  Aubrie A Harland; Larisa Yeomans; Nicholas W Griggs; Jessica P Anand; Irina D Pogozheva; Emily M Jutkiewicz; John R Traynor; Henry I Mosberg
Journal:  J Med Chem       Date:  2015-11-13       Impact factor: 7.446

7.  Nickel-Catalyzed Borylation of Benzylic Ammonium Salts: Stereospecific Synthesis of Enantioenriched Benzylic Boronates.

Authors:  Corey H Basch; Kelsey M Cobb; Mary P Watson
Journal:  Org Lett       Date:  2015-12-17       Impact factor: 6.005

8.  Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: applications toward the synthesis of calcimimetic agents.

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Journal:  J Org Chem       Date:  2013-05-13       Impact factor: 4.354

9.  Differential Binding of Rimantadine Enantiomers to Influenza A M2 Proton Channel.

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Journal:  J Am Chem Soc       Date:  2016-01-28       Impact factor: 16.383

10.  From racemic alcohols to enantiopure amines: Ru-catalyzed diastereoselective amination.

Authors:  Nathan J Oldenhuis; Vy M Dong; Zhibin Guan
Journal:  J Am Chem Soc       Date:  2014-08-29       Impact factor: 15.419
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