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

Stephen G. Davies*, Marcus J.C. Long, Andrew D. Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4536-4538
Number of pages3
JournalChemical Communications
Issue number36
DOIs
Publication statusPublished - 28 Sept 2005

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