18421-07-3Relevant academic research and scientific papers
Highly diastereoselective anti-dihydroxylation of 3-N,N- dibenzylaminocyclohex-1-ene N-oxide
Aciro, Caroline,Davies, Stephen G.,Kurosawa, Wataru,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.
, p. 1333 - 1336 (2009)
Oxidation of 3-N,N-dibenzylaminocyclohex-1-ene N-oxide in the presence of Cl3CCO2H proceeds with high levels of anti- diastereoselectivity (97% de), with no competing side reactions, allowing access to 1,2-anti-2,3-anti-3-aminocycloh
Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: Metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2- dihydroxycyclohexane
Davies, Stephen G.,Long, Marcus J. C.,Smith, Andrew D.
, p. 4536 - 4538 (2005)
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
Regioselective base-free intermolecular aminohydroxylations of hindered and functionalized alkenes
Ma, Zhiwei,Naylor, Bradley C.,Loertscher, Brad M.,Hafen, Danny D.,Li, Jasmine M.,Castle, Steven L.
, p. 1208 - 1214 (2012/03/11)
Regioselective base-free intermolecular aminohydroxylations of functionalized trisubstituted and 1,1-disubstituted alkenes employing benzoyloxycarbamate 3a and catalytic OsO4 are described. In all cases, the more substituted alcohol isomer is f
Ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes: Development of a metal-free dihydroxylation protocol
Aciro, Caroline,Claridge, Timothy D. W.,Davies, Stephen G.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.
supporting information; experimental part, p. 3751 - 3761 (2009/02/04)
Treatment of 3-aminocyclohex-1-enes with mCPBA in the presence of trichloroacetic acid gives the corresponding 1,2-anti-2,3-syn-1- trichloroacetoxy-2-hydroxy-3-aminocyclohexane with high levels of diastereoselectivity (90% de). This is consistent with a mechanism of oxidation involving hydrogen-bonded delivery of the oxidant by the allylic ammonium ion formed in situ, followed by highly regioselective ring-opening of the intermediate epoxide by trichloroacetic acid. The effect of conformational constraints upon the oxidation reaction is also examined. The Royal Society of Chemistry 2008.
Ammonium-directed dihydroxylation: Metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol
Aciro, Caroline,Davies, Stephen G.,Roberts, Paul M.,Russell, Angela J.,Smith, Andrew D.,Thomson, James E.
supporting information; experimental part, p. 3762 - 3770 (2009/02/04)
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-aminocyc
Stereocontrolled Preparation of Cyclohexane Amino Alcohols Utilising a Modified Mitsunobu Reaction
Sammes, Peter G.,Thetford, Dean
, p. 655 - 661 (2007/10/02)
A method for the introduction of amino groups into aliphatic systems is described.Cyclohex-2-enol reacts with aromatic diacylamines under Mitsunobu reaction conditions to give either N-alkylated or O-alkylated products in a controlled, predictable manner.
