944836-22-0

Upstream product

• 1255859-74-5 (S)-2-(2-(bis(4-trifluoromethyl-phenyl)phosphoryl))-5-(4-trifluoromethyl-phenyl)-4-tert-butyl-4,5-dihydro-oxazole 
• 1006709-00-7 C₁₄H₁₅BrF₃NO 
• 99665-68-6 potassium bis(4-(trifluoromethyl)phenyl)phosphide 
• 944836-38-8 (S)-2-(2-bromo-5-(trifluoromethyl)phenyl)-4-(tert-butyl)-4,5-dihydrooxazole 
• 13685-24-0 bis(4-trifluoromethylphenyl)phosphine chloride 
• 1483-55-2 2-bromo-5-trifluoromethylbenzonitrile 
• 112245-13-3 (S)-tert-leucinol 
• 944836-48-0 2-bromo-5-(trifluoromethyl)-benzoyl chloride 

Relevant academic research and scientific papers

Enantioselective construction of sterically hindered tertiary α-aryl ketones: A catalytic asymmetric synthesis of isoflavanones

A method for the catalytic asymmetric α-arylation of ketones bearing very sterically hindered aryl rings has been developed. This reaction occurs under mild conditions, in short reaction times and has been applied to the first catalytic asymmetric synthesis of isoflavanones.

Enantioselective decarboxylative alkylation reactions: Catalyst development, substrate scope, and mechanistic studies

α-Quaternary ketones are accessed through novel enantioselective alkylations of allyl and propargyl electrophiles by unstabilized prochiral enolate nucleophiles in the presence of palladium complexes with various phosphinooxazoline (PHOX) ligands. Excellent yields and high enantiomeric excesses are obtained from three classes of enolate precursor: enol carbonates, enol silanes, and racemic β-ketoesters. Each of these substrate classes functions with nearly identical efficiency in terms of yield and enantioselectivity. Catalyst discovery and development, the optimization of reaction conditions, the exploration of reaction scope, and applications in target-directed synthesis are reported. Experimental observations suggest that these alkylation reactions occur through an unusual inner-sphere mechanism involving binding of the prochiral enolate nucleophile directly to the palladium center. Sly as a PHOX: The development of an enantioselective decarboxylative palladium-catalyzed allylic alkylation reaction, utilizing phosphinooxazoline ligands, is described. The catalyst is applied to a range of allyl enol carbonate, silyl enol ether, and allyl β-ketoester substrates to provide alkylated ketone products in excellent yield and good ee (see scheme). The utility of these products is demonstrated by their use in several asymmetric syntheses. Mechanistic studies are reported suggesting an unusual inner-sphere mechanism. Copyright

A general enantioselective route to the chamigrene natural product family

Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and α-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented.

Rapid synthesis of an electron-deficient t-BuPHOX ligand: Cross-coupling of aryl bromides with secondary phosphine oxides

Herein an efficient and direct copper-catalyzed coupling of oxazoline-containing aryl bromides with electron-deficient secondary phosphine oxides is reported. The resulting tertiary phosphine oxides can be reduced to prepare a range of PHOX ligands. The p

A facile and modular synthesis of phosphinooxazoline ligands

The copper(I) iodide catalyzed phosphine/aryl halide coupling procedure of Buchwald et al. provides modular, robust, and scaleable access to phosphinooxazoline (PHOX) ligands. The advantages of this method are highlighted by the convenient synthesis of PH