37854-02-7Relevant academic research and scientific papers
On the dihydroxylation of cyclic allylic alcohols
Donohoe, Timothy J.,Garg, Rina,Moore, Peter R.
, p. 3407 - 3410 (1996)
The preparation and dihydroxylation (OsO4) of a series of conformationally constrained allylic alcohols is described. By using dichloromethane as solvent, the selectivity that favours the anti triol is substantially reduced by hydrogen-bonding
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.
