135214-52-7

Upstream product

• 108-05-4 vinyl acetate 
• 135107-04-9 (±)-(2-benzyloxiran-2-yl)methanol 
• 30457-89-7 2-benzylallyl alcohol 
• 1235457-88-1 (R)-2-benzyloxirane-2-carbaldehyde 
• 104-53-0 3-phenyl-propionaldehyde 
• 30457-88-6 2-benzyl-2-propenal 
• 933791-22-1 C₃H₈O₃C₇H₆C₇H₄O 
• 20593-63-9 2-Benzylacrylic acid ethyl ester 

Downstream Products

• 159701-46-9 2-methyl-3-phenylpropane-1,2-diol 
• 603109-97-3 Toluene-4-sulfonic acid (R)-2-benzyl-oxiranylmethyl ester 
• 1033409-52-7 C₁₂H₁₂Cl₃NO₂ 
• 603109-98-4 ((S)-1-Benzyl-spiro[2.4]hepta-4,6-dien-1-yl)-methanol 

Relevant academic research and scientific papers

Titanocene-Catalyzed Reductive Domino Epoxide Ring Opening/Defluorinative Cross-Coupling Reaction

Herein, we report a method for efficient synthesis of gem-difluorobishomoallylic alcohols starting from trifluoromethyl-substituted alkenes and epoxides via a titanocene-catalyzed reductive domino reaction, which consists of a Ti(III)-mediated radical-type ring opening and the following allylic defluorinative cross-coupling reaction via sequential radical addition and β-F elimination. Notably, complete regioselectivity and high tolerance of functionalities can be achieved in this reaction. Furthermore, diverse 6-fluoro-3,4-dihydro-2H-pyrans have been prepared through derivatization of the cross-coupling products in one single step.

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Chiral primary amine catalyzed asymmetric epoxidation of α-substituted acroleins

1,1-Disubstituted terminal alkenes remain challenging substrates in asymmetric epoxidation reactions. In this study, chiral primary amines are shown to catalyze the asymmetric epoxidation of α-substituted acroleins, a versatile type of 1,1-disubstituted t

Enantioselective formation of tert-alkylamines by desymmetrization of 2-substituted serinols

Novel enantioselective desymmetrization of 2-substituted 2-amino-1,3-propanediols has been established to generate asymmetric quaternary carbon centers comprising an amino group. Enantioselective as well as chemical conversion proved to be greatly dependent on the protecting group of the amino group in the substrate, desymmetrizing reagent, base, solvent, and naturally, catalyst. The highly effective desymmetrization has been implemented by using N-benzoylated substrates with benzoyl Chloride and triethylamine in the presence of tetraphenylbisoxazoline (24)-CuCl2 complex in THF at ambient temperature. An extensive survey of catalysts revealed that dimethylmalonate- bridged bisoxazoline-CuCl2 complexes were superior. Among them, the tetraphenylbisoxazoline (24)-CuCl2 complex turned out to work most efficiently with a wide array of the substrates. All the examined substrates, with the exception of 2-phenylserinol 36, were desymmetrized in the presence of 24-CuCl2 complex to give high enantioselectivities ranging from 85 to 95% ee. Complementary use of the diisopropylbisoxazoline (22)-CuCl2 complex has remedied the mediocre desymmetrization of 36 to give a significantly improved enantioselectivity from 63 to 83% ee.

Enantioselective synthesis of tertiary alcohols by the desymmetrizing benzoylation of 2-substituted glycerols

(Chemical Equation Presented) Complementary catalysts have been found for the enantioselective desymmetrization of 2-substituted glycerols by monobenzoylation with benzoyl chloride and Et3N to give chiral tertiary alcohols with 80 to 94% ee (se

Dipodal ligands from chiral spiro[2.4]hepta-4,6-dienes: Solid state conformational effects by tether substitution in dipodal η5,η1-CpP-ruthenium(II) complexes

New chiral spiro[2.4]hepta-4,6-dienes were prepared and used in an efficient synthesis of cyclopentadienyl ruthenium complexes with pendant phosphine donors. Solid state structures reveal a conformation trend among three structurally homologous complexes