86423-92-9Relevant articles and documents
Asymmetric hydrogenation of allylic alcohols using ir?N,P-Complexes
Li, Jia-Qi,Liu, Jianguo,Krajangsri, Suppachai,Chumnanvej, Napasawan,Singh, Thishana,Andersson, Pher G.
, p. 8342 - 8349 (2018/05/23)
In this study, a series of γ,γ-disubstituted and β,γ-disubstituted allylic alcohols were prepared and successfully hydrogenated using suitable N,P-based Ir complexes. High yields and excellent enantioselectivities were obtained for most of the substrates studied. This investigation also revealed the effect of the acidity of the N,P?Ir-complexes on the acid-sensitive allylic alcohols. DFT ΔpKa calculations were used to explain the effect of the N,P-ligand on the acidity of the corresponding Ir-complex. The selectivity model of the reaction was used to accurately predict the absolute configuration of the hydrogenated alcohols.
Total synthesis, proof of absolute configuration, and biosynthetic origin of stylopsal, the first isolated sex pheromone of strepsiptera
Lagoutte, Roman,?ebesta, Petr,Jiro?, Pavel,Kalinová, Blanka,Jiro?ová, Anna,Straka, Jakub,?erná, Kate?ina,?obotník, Jan,Cva?ka, Josef,Jahn, Ullrich
supporting information, p. 8515 - 8524 (2013/07/11)
The asymmetric total synthesis of the diastereomers of stylopsal establishes the absolute configuration of the first reported sex pheromone of the twisted-wing parasite Stylops muelleri as (3R,5R,9R)-trimethyldodecanal. The key steps for the diastereo- and enantiodivergent introduction of the methyl groups are two different types of asymmetric conjugate addition reactions of organocopper reagents to α,β-unsaturated esters, whereas the dodecanal skeleton is assembled by Wittig reactions. The structure of the natural product was confirmed by chiral gas chromatography (GC) techniques, GC/MS and GC/electroantennography (EAD) as well as field tests. An investigation into the biosynthesis of the pheromone revealed that it is likely to be produced by decarboxylation of a 4,6,10-trimethyltridecanoic acid derivative, which was found in substantial amounts in the fat body of the female, but not in the host bee Andrena vaga. This triple-branched fatty acid precursor thus seems to be biosynthesized de novo through a polyketide pathway with two consecutive propionate-propionate-acetate assemblies to form the complete skeleton. The simplified, motionless and fully host-dependent female exploits a remarkable strategy to maximize its reproductive success by employing a relatively complex and potent sex pheromone. Love at first.i??-smell: An asymmetric total synthesis, gas chromatographic analyses, and field tests confirm the structure of the first isolated sex pheromone of a twisted-wing parasite Stylops muelleri (see figure). Its biosynthetic origin and complexity demonstrate the considerable efforts undertaken by the motionless and fully host-dependant female to attract the very short-lived free-living male, thus securing success in the perpetuation of the species. Copyright
Asymmetric conjugate addition for the preparation of syn-1,3-dimethyl arrays: Synthesis and structure elucidation of capensifuranone
Williams, David R.,Nold, Andrea L.,Mullins, Richard J.
, p. 5374 - 5382 (2007/10/03)
The synthesis of capensifuranone (1) has been achieved by the application of developments for asymmetric conjugate addition reactions of organocopper reagents with nonracemic N-enoyl-4-phenyl-1,3-oxazolidinones for the preparation of 1,3-syn-dimethyl arra
