6319-19-3Relevant academic research and scientific papers
SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one
Bull, Steven D.,Davies, Stephen G.,Garner, A. Christopher,Kruchinin, Dennis,Key, Min-Suk,Roberts, Paul M.,Savory, Edward D.,Smith, Andrew D.,Thomson, James E.
, p. 2945 - 2964 (2008/02/09)
The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions. The Royal Society of Chemistry 2006.
Decarbonylative cross-coupling of cyclic anhydrides: Introducing stereochemistry at an sp3 carbon in the cross-coupling event
O'Brien, Erin M.,Bercot, Eric A.,Rovis, Tomislav
, p. 10498 - 10499 (2007/10/03)
Treatment of cyclic anhydrides with stoichiometric amounts of nickel-neocuproine complex generates alkylcarboxylato-nickelalactones upon extrusion of CO. These metalacycles undergo cross-coupling with arylzinc reagents. The generated CO is sequestered in situ by a nickel-dppb complex. The overall sequence effects a secondary sp3(electrophile)-sp2(nucleophile) cross-coupling and allows for control of stereochemistry during the bond-forming event. Copyright
Enzymatic kinetic resolution of aromatic substituted norbornene mono-esters using pig's liver esterase
Mamaghani
, p. 147 - 151 (2007/10/03)
Pig's liver esterase (PLE) has been used as a chiral catalyst in the enzymatic kinetic resolution of aromatic substituted norbornene mono-esters, methyl 3-endo-phenylbicyclo[2.2.1]hept-5-ene-2-exo-carboxylate and its endo-counterpart, methyl 3-endo-p-nitro-phenyl-bicyclo[2.2.1]hept-5-ene-2-exo-carboxylate and methyl 3-endo-benzoylbicyclo[2.2.1]hept-5-ene-2-exo-carboxylate. In this study a range of low to high enantioselectivities (83% ee) was observed. The effect of co-solvents has also been examined.
Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-(Aminomethyl)-3-phenylbicyclo [2.2.2]- and - [2.2.1] alkane dopamine uptake inhibitors
Deutsch, Howard M.,Collard, David M.,Zhang, Liang,Burnham, Kikue S.,Deshpande, Abhay K.,Holtzman, Stephan G.,Schweri, Margaret M.
, p. 882 - 895 (2007/10/03)
As part of a program to develop site-specific medications for cocaine abuse, a series of 2-(aminomethyl)-3-phenylbicyclo[2.2.2]- and -[2.2.1]alkane derivatives was synthesized and tested for inhibitory potency in [3H]WIN 35,428 binding and [3H]dopamine uptake assays using rat striatal tissue. Selected compounds were tested for their ability to substitute for cocaine in rat drug discrimination tests. Synthesis was accomplished by a series of Diels-Alder reactions, using cis- and trans-cinnamic acid derivatives (nitrile, acid, acid chloride) with cyclohexadiene and cyclopentadiene. Standard manipulations produced the aminomethyl side chain. Many of the compounds bound with high affinity (median IC50 = 223 nM) to the cocaine binding site as marked by [3H]WIN 35,428. Potency in the binding assay was strongly enhanced by chlorine atoms in the 3- and/or 4-position on the aromatic ring and was little affected by corresponding methoxy groups. In the [2.2.2] series there was little difference in potency between cis and trans compounds or between N,N-dimethylamines and primary amines. In the [2.2.1] series the trans exo compounds tended to be least potent against binding, whereas the cis exo compounds were the most potent (4-Cl cis exo: IC50 = 7.7 nM, 27-fold more potent than 4-Cl trans-exo). Although the potencies of the bicyclic derivatives in the binding and uptake assays were highly correlated, some of the compounds were 5-7-fold less potent at inhibiting [3H]-dopamine uptake than [3H]WIN 35,428 binding (for comparison, cocaine has a lower discrimination ratio (DR) of 2.5). The DR values were higher for almost all primary amines and for the trans-[2.2.2] series as compared to the cis-[2.2.2]. Most of the compounds had Hill coefficients approaching unity, except for the [2.2.2] 3,4-dichloro derivatives, which all had n(H) values of about 2.0. Two of the compounds were shown to fully substitute for cocaine in drug discrimination tests in rats, and one had a very long duration of action.
Saccharomyces cerevisiae in the catalysis of cycloaddition reactions
Rao, K Rama,Bhanumathi, N,Nageswar, Y V D,Srinivasan, T N
, p. 937 - 938 (2007/10/02)
A brief review of the preliminary results of the biocatalytic cycloaddition reaction of cyclopentadiene 1, vinylpyridine 9 and pyridazinone 12 with various dienophiles in the presence of Saccharomyces cerevisiae is presented.
A stereoselective biocatalytic Diels-Alder reaction
Rao,Srinivasan,Bhanumathi
, p. 5959 - 5960 (2007/10/02)
Baker's yeast catalyzes the stereoselective Diels-Alder reaction of cyclopentadiene 1 with dienophiles 2, 4 and 6. A predominant formation of exo isomer is observed in some cases.
A NEW CATALYTIC PROCESS BASED ON SEQUENTIAL INSERTION OF STRAINED OLEFINS AND CARBON MONOXIDE INTO Pd-C BONDS.
Catellani, Marta,Chiusoli, Gian Paolo,Peloso, Cesare
, p. 813 - 816 (2007/10/02)
A palladium-catalyzed synthesis of carboxylic acids, esters and anhydrides by sequential alkylation, vinylation or arylation and carbonylation of strained olefins is reported.
