130822-25-2Relevant academic research and scientific papers
Stereoselective Reduction of δ-Hydroxy-β-ketoesters
Kathawala, Faizulla G.,Prager, Bernhard,Prasad, Kapa,Repic, Oljan,Shapiro, Michael J.,et al.
, p. 803 - 805 (1986)
The reduction of δ-hydroxy-β-ketoesters 1 was investigated with three different reducing agents.In several instances, high selectivity in favor of syn-1,3-diols was observed.
Diastereoselective hydrogenation of 1,3-hydroxyketones
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Page 5, (2008/06/13)
The invention relates to a novel process of diastereoselective hydrogenation of 1,3-hydroxyketones of formula (I) wherein R, R′ and R″ are as defined in claim 1 which is carried out in a solvent in the presence of a magnesium salt, a heterogeneous platinu
Studies on the stereoselective selenolactonization, hydroxy and methoxy selenenylation of α- and β-hydroxy acids and esters. Synthesis of δ- and γ-lactones
Aprile, Carmela,Gruttadauria, Michelangelo,Amato, Maria E.,D'Anna, Francesca,Lo Meo, Paolo,Riela, Serena,Noto, Renato
, p. 2241 - 2251 (2007/10/03)
The diastereoselective synthesis of hydroxy substituted γ- and δ-lactones was accomplished following two approaches. A 5- or 6-endo cyclization promoted by electrophilic selenium reagents of α- or β-hydroxy acids and a 5- or 6-exo cyclization of hydroxy esters obtained through a diastereoselective hydroxy selenenylation reaction of α- or β-hydroxy esters. Moreover, the diastereoselective methoxy selenenylation of the above compounds was investigated showing a case in which the compound that was unreactive in the hydroxy selenenylation conditions gave, in the methoxy selenenylation conditions, the deprotected diol. The usefulness of the methoxy selenenylation procedure was proven by the preparation of a symmetric compound unsymmetrically functionalized. Yields and selectivities were found to depend on substituents (Ph or alkyl groups at the carbon atom that undergoes the nucleophilic attack), mode of cyclization, kinetic or thermodynamic control conditions. In the latter case, silica gel played an important role.
Stereocontrolled approach to δ- and γ-lactones and 1,3-diols. The role of X- ion in the selenolactonization
Gruttadauria, Michelangelo,Aprile, Carmela,Noto, Renato
, p. 1669 - 1672 (2007/10/03)
Two complementary approaches have been realized for the stereoselective synthesis of 4,6-disubstituted δ-lactones and 1,3-anti and syn diols. In the 6-endo selenolactonization the role of the X- ion on the stereoselectivity is shown. Moreover,
Stereoselective Syntheses of α-Substituted Cyclic Ethers and syn-1,3-Diols
Homma, Koichi,Takenoshita, Haruhiro,Mukaiyama, Teruaki
, p. 1898 - 1915 (2007/10/02)
In the presence of a catalytic amount of triphenylmethylium hexachloroantimonate or a catalyst system of antimony pentachloride, chlorotrimethylsilane and tin(II)iodide, α-substituted cyclic ethers are stereoselectively prepared from lactones by successiv
