98278-17-2Relevant academic research and scientific papers
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.
, p. 3762 - 3770 (2008)
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
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.
supporting information; scheme or table, 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
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.
supporting information; experimental part, p. 1333 - 1336 (2009/09/27)
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 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 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 (2007/10/03)
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
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.
