2218-15-7Relevant articles and documents
Enantioselective reduction of α-substituted ketones mediated by the boronate ester TarB-NO2
Eagon, Scott,Ball-Jones, Nicholas,Haddenham, Dustin,Saavedra, Jaime,Delieto, Cassandra,Buckman, Matthew,Singaram, Bakthan
supporting information; experimental part, p. 6418 - 6421 (2010/12/30)
A facile and mild reduction procedure is reported for the preparation of chiral secondary alcohols prepared from α-substituted ketones using sodium borohydride and the chiral boronate ester (l)-TarB-NO2. Direct reduction of substituted ketones bearing Lewis basic heteroatoms generally provided secondary alcohols of only modest enantiomeric excess likely due to either competition between the target carbonyl and the functionalized sidechains at the Lewis acidic boron atom in TarB-NO2 or the added steric bulk of the α-sidechain. As an alternative method, these substrates were synthesized using TarB-NO2 via a two-step procedure involving the reduction of an α-halo ketone to a chiral terminal epoxide, followed by regioselective/regiospecific epoxide opening by various nucleophiles. This procedure provides access to a variety of functionalized secondary alcohols including β-hydroxy ethers, thioethers, nitriles, and amines with enantiomeric excesses of 94% and yields up to 98%.
Synthesis and Biological activity of kappa opioid receptor agonists. Part 2: Preparation of 3-aryl-2-pyridone analogues generated by solution- and solid-phase parallel synthesis methods
Semple, Graeme,Andersson, Britt-Marie,Chhajlani, Vijay,Georgsson, Jennie,Johansson, Magnus J.,Rosenquist, Asa,Swanson, Lars
, p. 1141 - 1145 (2007/10/03)
New analogues of the previously described 3-aryl pyridone KOR agonists have been synthesised by parallel synthetic methods, both in solution- and with solid-phase chemistry, making use of the well known and versatile Mitsunobu, Suzuki and Buchwald reactions. Opioid receptor binding data for the compounds produced is reported.
Studies on the Oxidation of Enamines with Molecular Oxygen. III Oxidation of Some Amino Styrenes
Blau, K.,Burgemeister, I.,Grasnick, J.,Voerckel, V.
, p. 455 - 466 (2007/10/02)
In the oxidation of the amino styrenes 1a - 1j only products of the oxidative attack at the C=C double bond and hydrolysis products are obtained.Aprotic dipolar solvents and the addition of molecular sieve 5A promote the oxygen uptake.The addition of hydroquinone to the oxidation system does not influence the rate of oxygen absorption or the yields of the oxidation products.