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1,3-Stereoinduction in the addition of alkyl radicals to glyoxylic imines derived from various chiral amines has been investigated. New synthetic methodologies involving Et 3 B and Et 2 Zn as mediators have been compared. Dihydro-1,4-oxazin-2-one ( 2b ) gave the highest d.e. but no...
When carboxylic acids β-substituted by a tert -butoxy group were treated with thionyl chloride, an intermediate acyl chloride β-substituted by a hydroxyl group was likely formed. Its subsequent intramolecular cyclization produced novel β-lactones in one step. Two enantiomerically enriched...
New α-phosphono-β-aryl- or β-heteroaryl-substituted α,β-unsaturated dithioesters 2 were easily prepared from diethyl phosphonodithioacetate 1 and used as thiadienes in thermal or high pressure hetero Diels–Alder cycloadditions with enol and thioenol ethers. The resulting new phosphono...
(2- 13 C)-Quercetin-4′- O -β-glucoside was synthesised in four steps and 28% yield from barium ( 13 C)-carbonate. This short route will be applicable to the synthesis of radiolabelled quercetin-4′- O -β- d -glucoside from barium ( 14 C)-carbonate. The most important feature is control of...
In aqueous acetonitrile with FeCl 2 or hemin/ l -cysteine, a peroxide ( 4 ) obtained from abietic acid by photosensitized air oxidation undergoes rearrangement to give a diepoxide and two spiro compounds as major products.
Ortho -(2-triethoxysilylethyl) derivatives of aryl ketones undergo oxidative desilylation with H 2 O 2 . Tetralone derivatives have served as model substrates for 14-2-(triethoxysilylethyl)-7-oxopodocarpanes, which have been converted into 2-arylethanols in a four-step sequence (BH 3 ·BMS, H 2 O...
The free base 2,4-bis-(1′-dodecynyl)-deuteroporphyrin IX dioctylester, 6a , its Zn(II)complex, Zn - 6a , its Cu(II)complex, Cu - 6a , its Ni(II)complex, Ni - 6a and a number of related compounds have been prepared. The synthesis of 6a involves as key steps the palladium-catalyzed coupling of...
N -Substituted 4-methylene-2-isoxazolidinones 9a – 9e have been prepared from the tandem condensation of isocyanates 3 with α-ketol 7 . In a more polar solvent (DMF) the same reaction led to stereoisomeric alcohols 11 and 12 , which could be transformed to the thermodynamically more stable...
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