15763-62-9Relevant articles and documents
Synthesis of α-difluoro and α-difluoro-β-trifluoroketo-derivatives as potential inhibitors for cholesterol ester hydrolase
David, Beatrice,Schuber, Francis
, p. 1673 - 1676 (1996)
Pancreatic Cholesterol Ester Hydrolase, a serine esterase, catalyzes the hydrolysis of cholesteryl esters in the gut. We report the convergent synthesis of α-difluoro-β-trifluoroketo-(5,10,15) and of α-difluoroketo-derivatives (22,23) as inhibitors of this enzyme that were designed to generate stable tetrahedral reaction intermediates.
Palladium-catalyzed reduction of carboxylic acids to aldehydes with hydrosilanes in the presence of pivalic anhydride
Fujihara, Tetsuaki,Cong, Cong,Terao, Jun,Tsuji, Yasushi
supporting information, p. 3420 - 3424 (2013/12/04)
A palladium catalyst system that allows the reduction of carboxylic acids to the corresponding aldehydes with hydrosilanes as reducing agent and pivalic anhydride as an indispensable reagent has been developed. A simple mixture of commercially available bis(dibenzylideneacetone)palladium(0) [Pd(dba) 2], tri(para-tolyl)phosphane and methylphenylsilane realized the reduction of various aliphatic carboxylic acids as well as benzoic acids to aldehydes in good to high yields. Copyright
Stereoselective synthesis of cyclopropanes based on a 1,2-chirality transfer
Muehling, Olaf,Wessig, Pablo
supporting information; experimental part, p. 7951 - 7960 (2009/10/23)
A stereoselective route to enantiomerically enriched bicyclic cyclopropane derivatives 13 is described which is based on a conceptually novel 1,2-chirality transfer approach. The hyperconjugative interaction of an electronically excited carbonyl group with the σ* orbital of an adjacent C-X bond in the transition state of a hydrogen abstraction causes the preference of a certain conformation and consequently the differentiation between two diastereotopic methylene groups. The 1,2-chirality transfer is completed by a subsequent HX elimination which destroys the only stereogenic center in the reactants 12. Furthermore, it was found that contrary enthalpic and entropic influences result in the existence of an inversion temperature T0. Upon crossing T0 the stereoselectivity is reversed. Considering this temperature dependency, chirality transfer efficiencies of up to 83% could be achieved. The absolute configuration of most products could be unambiguously determined by VCD spectroscopy combined with DFT calculations.
