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Issue 36, 2005
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Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane

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Abstract

Treatment of N,N-dibenzylaminocyclohex-2-ene with mCPBA in the presence of CCl3CO2H gives 1,2-anti-2,3-syn-1-trichloroacetoxy-2-hydroxy-3-N,N-dibenzylaminocyclohexane with high diastereoselectivity; this methodology has been used to facilitate the metal-free stereoselective syntheses of all the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane.

Graphical abstract: Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane

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Publication details

The article was received on 29 Jun 2005, accepted on 18 Jul 2005 and first published on 09 Aug 2005


Article type: Communication
DOI: 10.1039/B509088A
Citation: Chem. Commun., 2005,0, 4536-4538
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    Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane

    S. G. Davies, M. J. C. Long and A. D. Smith, Chem. Commun., 2005, 0, 4536
    DOI: 10.1039/B509088A

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