Showing papers by "Min Xu published in 2008"
TL;DR: In this paper, a chiral trifluoromethyl quaternary carbon center of dihydroquinazoline was constructed by an asymmetric Mannich reaction and chiral recognition.
Abstract: The highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by an asymmetric Mannich reaction and chiral recognition are described The key transformation was to establish the chiral trifluoromethyl quaternary carbon center by a diamine-Bronsted acid-catalyzed enantioselective and regioselective Mannich reaction of a methyl ketone and 4-trifluoromethyldihydroquinazoline An unusual phenomenon of self-discrimination of enantiomers in hydrogen-bonded dimers was observed A valuable intermediate was transformed into the enantiopure HIV reverse transcriptase inhibitor DPC 083 (>999 ee) simply by reduction of the carbonyl group and elimination of the hydroxy group in hexamethylphosphoric tramide (HMPA)
76 citations
TL;DR: An efficient approach for synthesizing a series of 2-sulfide carbapenems has been developed using two successive Cu(I)-catalyzed cross-couplings in a single pot.
53 citations
TL;DR: A novel and convenient protocol for synthesis of alpha-haloacrylates starting from phosphonium ylide and aldedyde or alcohol was described, and good yield as well as a high Z/E ratio were shown in representative cases.
27 citations
TL;DR: Six new iridoidal glucosides, 2′-O-(3″-hydroxybenzoyl)-8-epikingiside, kingiside (10), secologanoside (11), secoxyloganin (12), and alpigenoside (13), were isolated from the whole plant of Gentiana rhodantha (Gentianaceae).
22 citations
TL;DR: In this paper, the chiral trifluoromethyl quaternary carbon center of dihydroquinazoline was constructed by an asymmetric Mannich reaction and chiral recognition.
Abstract: The highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by an asymmetric Mannich reaction and chiral recognition are described. The key transformation was to establish the chiral trifluoromethyl quaternary carbon center by a diamine-Bronsted acid-catalyzed enantioselective and regioselective Mannich reaction of a methyl ketone and 4-trifluoromethyldihydroquinazoline. An unusual phenomenon of self-discrimination of enantiomers in hydrogen-bonded dimers was observed. A valuable intermediate was transformed into the enantiopure HIV reverse transcriptase inhibitor DPC 083 (>99.9 ee) simply by reduction of the carbonyl group and elimination of the hydroxy group in hexamethylphosphoric tramide (HMPA).
Patent•
01 Apr 2008
TL;DR: In this paper, the authors propose a method to combine compositions pharmaceutiques, des procedes de preparation des composes, des intermediaires synthetiques, and des procedures d'utilisation des compositions, independamment ou en combinaison avec d'autres agents therapeutiques.
Abstract: L'invention concerne des composes ayant un effet inhibiteur sur le cotransporteur de glucose dependant du sodium SGLT. L'invention concerne egalement des compositions pharmaceutiques, des procedes de preparation des composes, des intermediaires synthetiques et des procedes d'utilisation des composes, independamment ou en combinaison avec d'autres agents therapeutiques, pour traiter des maladies ou affections qui sont affectees par l'inhibition du SGLT.
TL;DR: In this paper, a protocol for α-haloacrylates starting from aldedyde or alcohol was described, and good yield as well as a high Z/E ratio were shown in representative cases.
Abstract: A novel and convenient protocol for synthesis of α-haloacrylates starting from phosphonium ylide and aldedyde or alcohol was described. Halodimethylsulfonium halide was used for the first time in halogenation of phosphonium ylide. Good yield as well as a high Z/E ratio were shown in representative cases, and an umpolung dimethyl sulfide−ylide species might be involved as an intermediate.
TL;DR: In this paper, an efficient approach for synthesizing a series of 2-sulfide carbapenems was developed using two successive Cu(I)-catalyzed cross-couplings in a single pot.
Abstract: An efficient approach for synthesizing a series of 2-sulfide carbapenems has been developed using two successive Cu(I)-catalyzed cross-couplings in a single pot. The method involves highly selective intramolecular coupling of lactam and dihaloalkene using 2,2'-bipyridine as a ligand, followed by intermolecular C-S formation in the presence of another ligand (1,10-phenanthroline, PPh3) and mercaptan.