Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol.
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.
Aciro
Caroline
C
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.
Davies
Stephen G
SG
Roberts
Paul M
PM
Russell
Angela J
AJ
Smith
Andrew D
AD
Thomson
James E
JE
D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry; D003514:Cyclohexylamines / Q000138:chemical synthesis* / Q000737:chemistry; D006878:Hydroxides / Q000737:chemistry*; D006900:Hydroxylation; D008670:Metals / Q000737:chemistry; D010084:Oxidation-Reduction; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
C533263:3-aminocyclohexane-1,2-diol; D003511:Cyclohexanols; D003514:Cyclohexylamines; D006878:Hydroxides; D008670:Metals; D000644:Quaternary Ammonium Compounds; C031356:hydroxide ion