Literature DB >> 18843406

Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol.

Caroline Aciro1, Stephen G Davies, Paul M Roberts, Angela J Russell, Andrew D Smith, James E Thomson.   

Abstract

The ammonium-directed, metal-free oxidation of 3-(N,N-dibenzylamino)cyclohex-1-ene with mCPBA in the presence of either trichloroacetic acid or tosic acid has been used as the key step to facilitate the synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol, in >98% de in each case.

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Year:  2008        PMID: 18843406     DOI: 10.1039/b808812h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  3 in total

1.  Hf(IV)-catalyzed enantioselective epoxidation of N-alkenyl sulfonamides and N-tosyl imines.

Authors:  José Luis Olivares-Romero; Zhi Li; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2012-03-20       Impact factor: 15.419

2.  Regio- and Diastereoselective Synthesis of Highly Substituted, Oxygenated Piperidines from Tetrahydropyridines.

Authors:  Shuming Chen; Brandon Q Mercado; Robert G Bergman; Jonathan A Ellman
Journal:  J Org Chem       Date:  2015-06-22       Impact factor: 4.354

3.  Regio- and stereoselective synthesis of new diaminocyclopentanols.

Authors:  Evgeni A Larin; Valeri S Kochubei; Yuri M Atroshchenko
Journal:  Beilstein J Org Chem       Date:  2014-10-28       Impact factor: 2.883

  3 in total

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