10136-65-9Relevant articles and documents
ASYMMETRIC SYNTHESIS OF (+)-PHOSPHINOTHRICIN and (+)-2-AMINO-4-PHOSPHONOBUTYRIC ACID
Minowa, Nobuto,Hirayama, Masao,Fukatsu, Shunzo
, p. 1147 - 1150 (1984)
Asymmetric synthesis of (+)-phosphinothricin, (+)-2-amino-4-phosphono-butyric acid, and their enantiomers has been achieved by the Michael addition of chiral glycine Schiff bases to vinyl phosphorus compounds.
Chiral Titanium(IV) Complexes Containing Polydentate Ligands Based on α-Pinene. Catalytic Activity in Sulfoxidation with Hydrogen Peroxide
Reviejo, Irene,Tabernero, Vanessa,Mosquera, Marta E. G.,Ramos, Javier,Cuenca, Tomás,Jiménez, Gerardo
, p. 3437 - 3449 (2018)
The reaction of TiCl4-n(OiPr)n (n = 0, 2, 4) with various terpenoid preligands based on α-pinene, C7H6Me3(OH)(NCH2CH2G) (G = NH2, I; NHMe, II; OH, III), stereoselectively affords a series of new chiral titanium(IV) complexes. Such complexes are either octahedral, [TiCl2X(OC7H6Me3NCH2CH2G-κ3N,N,O)] (X = Cl, G = NH2, 1; X = OiPr, G = NH2, 2; G = NHMe, 3), or trigonal bipyramidal, [Ti(OiPr)3(OC7H6Me3NCH2CH2G-κ2N,O)] (G = NH2, 4; NHMe, 5) and [TiX(OiPr)(OC7H6Me3NCH2CH2O-κ3N,O,O?)] (X = Cl, 6; OiPr, 8), depending on the acidity of titanium, the reaction conditions and the nature of the pendant ending group of the terpenoid ligand. Density functional theory (DFT) calculations have been carried out to assess the stability of the multiple possible diastereoisomers allowing us to propose structural suggestions. The new titanium complexes efficiently catalyze the selective oxidation of various types of sulfides to either sulfoxides or sulfones using aqueous hydrogen peroxide, under mild conditions. All compounds have been characterized by multinuclear NMR spectroscopy and the molecular structure for some of them has been determined by X-ray diffraction.
Novel access to verbenone via ruthenium nanoparticles-catalyzed oxidation of Α-pinene in neat water
Rauchdi, Mariem,Ait Ali, Mustapha,Roucoux, Alain,Denicourt-Nowicki, Audrey
, p. 266 - 273 (2018)
Aqueous suspensions of Ru(0) nanoparticles, stabilized with hydroxyethylammonium salts and possessing sizes around 2 nm, proved to be active and selective in the mild oxidation of α-pinene in the presence of tert-butylhydroperoxide, in neat water. Verbenone, a product of great interest for fine chemistry, was obtained as major product with yield up to 41% under optimized conditions. 2-hydroxy-3-pinanone was identified as a co-product of the reaction, but with very low amount (7%). Kinetic investigations allowed determining the potential reaction intermediates and by-products. Moreover, mechanistic studies with radical scavengers confirmed that α-pinene oxidation mainly implies both carbon- and oxygen-centered radicals.
A practical method for preparation of optically pure oxazaborolidines from α-pinene
Masui, Moriyasu,Shioiri, Takayuki
, p. 8363 - 8370 (1995)
(1S,2S,3R,5S)- and (1S,2S,3R,5S)-3-amino-2-hydroxypinane (1 and 2) were prepared from the corresponding α-pinene in optically pure form. They and their derivatives reacted with various organoborane compounds. A variety of chiral oxazaborolidines 3a-e and 4 were obtained in high yield.
Evidence for the existence of a cyclic ruthenium (VI) diester as an intermediate in the oxidative scission of (-)-α-pinene with RuO4
Albarella, Laura,Giordano, Federico,Lasalvia, Maria,Piccialli, Vincenzo,Sica, Donato
, p. 5267 - 5270 (1995)
The reaction of (-)-α-pinene (1) with RuO4 in CCl4 at room temperature affords the ketoaldehyde 3 as the sole product. Evidence is reported that the oxidative scission of the olefinic substrate to 3 proceeds through a ruthenium (VI) diester intermediate for which we propose structure 2 on the basis of spectral evidence and comparison with the osmium-containing analogue of 2, synthesised by reaction of (-)-α-pinene with OsO4 in dioxane and whose structure has been determinated by single crystal X-ray diffraction analysis. Compound 2 was also shown to be an intermediate compound in the RuO4 oxidation of (-)-α-pinene performed in acetone-water (2:1) which gives α-ketol 4 as the sole oxidation product.
Synthesis and characterization of new palladium complexes based on polydentate chiral Schiff base and amines ligands derived from (+)-2-hydroxypinan-3-one
Gur'eva, Yana A.,Alekseev, Igor N.,Dvornikova, Irina A.,Zalevskaya, Olga A.,Kuchin, Aleksandr V.
, p. 300 - 305 (2018/11/21)
Seven novel palladium complexes of the type [Pd(HL)Cl2] and [Pd(L)Cl] containing chiral pinane ligands (HL = 3-[(2-aminoethyl)imino]-pinane-2-ol; 3,3′-(ethylenediimino)bis-pinane-2-ol; cis-3-(2-aminoethylamino)-pinane-2-ol; cis-3,3′(ethylenediamino)bis-pinane-2-ol; trans-3,3′(ethylenediamino)bis-pinane-2-ol; 3-[2-(2-hydroxybenzylamino)ethylamino]-pinane-2-ol; L = 3-[2-(3,5-di-tert-butyl-2-hydroxybenzylidene)aminoethylimino]pinane-2-ol) were synthesized in good yields from the direct reaction of chiral nitrogen ligands with Li2PdCl4 in MeOH. These synthesized complexes were characterized by means of elemental analysis, FT-IR, multidimensional and multinuclear NMR spectroscopic methods.
