118629-70-2

Upstream product

• 113826-06-5 (R)-glycidyl tosylate 
• 591-51-5 phenyllithium 
• 20312-36-1 L-3-phenyllactic acid 
• 104-53-0 3-phenyl-propionaldehyde 
• 17131-14-5 (S)-(-)-3-phenyl-1,2-propanediol 
• 98-59-9 p-toluenesulfonyl chloride 
• 121958-41-6 [(2R,3R)-3-phenyloxiran-2-yl]methyl 4-methylbenzenesulfonate 
• 771476-48-3 (S)-3-phenyl-2-(N-phenyl-aminooxy)-propan-1-ol 

Downstream Products

• 91420-74-5 (S)-(2,3-epoxypropyl)benzene 
• 61393-94-0 (R)-2-benzyloxirane 

Relevant academic research and scientific papers

Synthesis of Seven-Membered Benzolactones by Nickel-Catalyzed C?H Coupling of Benzamides with Oxetanes

A NiCl2(PEt3)2-catalyzed regioselective C?H coupling of 8-aminoquinoline-derived benzamides with oxetanes has been developed. The reaction proceeds with concomitant removal of the 8-aminoquinoline auxiliary to directly for

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS AND THE USES THEREOF

The invention relates to pyridinyl nicotinic acetylcholine receptor ligands, compositions comprising an effective amount of a pyridinyl nicotinic acetylcholine receptor ligand and methods to treat or prevent a condition, such as depression and nicotine dependence, comprising administering to an animal in need thereof an effective amount of a pyridinyl nicotinic acetylcholine receptor ligand.

The direct catalytic asymmetric α-aminooxylation reaction: Development of stereoselective routes to 1,2-diols and 1,2-amino alcohols and density functional calculations

Proline-catalyzed direct asymmetric α-aminooxylation of ketones and aldehydes is described. The proline-catalyzed reactions between unmodified ketones or aldehydes and nitrosobenzene proceeded with excellent diastereo- and enantioselectivities. In all cases tested, the corresponding products were isolated with > 95% ees. Methyl alkyl ketones were regiospecifically oxidized at the methylene carbon atom to afford enantiomerically pure α-aminooxylated ketones. In addition, cyclic ketones could be α,α′-dioxidized with remarkably high selectivity, furnishing the corresponding diaminooxylated ketones with > 99% ees. The reaction mechanism of the proline-catalyzed direct asymmetric α-aminooxylation was investigated, and we performed density functional theory (DFT) calculations in order to investigate the nature of the plausible transition states further. We also screened other organocatalysts for the asymmetric α-oxidation reaction and found that several proline derivatives were also able to catalyze the transformation with excellent enantioselectivities. Moreover, stereoselective routes for the synthesis of monoprotected vicinal diols and hydroxyketones were found. In addition, short routes for the direct preparation of enantiomerically pure epoxides and 1,2-amino alcohols are presented. The direct catalytic α-oxidation is also a novel route for the stereoselective preparation of β-adrenoreceptor antagonists.

Chemoselective reduction of 2,3-epoxy tosylates with DIBAL-H as a general route to enantiomerically-enriched 1-tosyloxy-2-alkanols

2,3-Epoxy tosylates may be reduced with DIBAL-H in CH2Cl2 or ether at -40°C to 1-tosyloxy-2-alkanols in high (94-98%) yields.

Arenesulfonate Derivatives of Homochiral Glycidol: Versatile Chiral Building Blocks for Organic Synthesis

The preparation of a series of crystalline arenesulfonate derivatives of enantiomerically enriched glycidol is described.The enhancement of optical purity by recrystallization was particularly successful for two of these derivatives, glycidyl tosylate and glycidyl 3-nitrobenzenesulfonate, which were obtained in 97 percent ee and 99 percent ee, respectively.Very high regioselectivity was observed in the reactions of these compounds with a variety of nucleophiles, including aryl oxides, Et2AlCN, organometallic reagents, and BH3-NaBH4.The application of this methodology to the synthesis of homochiral β-adrenergic blocking agents and homochiral terminal epoxides is discussed.