80691-79-8

Upstream product

• 16251-77-7 3-Phenylbutyraldehyde 
• 2722-36-3 3-phenyl-1-butanol 
• 80691-80-1 2-(1-phenylethyl)propane-1,3-diol 
• 1115-11-3 2-methyl-2-pentenal 
• 98-80-6 phenylboronic acid 
• 50-00-0 formaldehyd 

Downstream Products

• 1235457-91-6 (S)-2-((R)-1-phenylethyl)oxirane-2-carbaldehyde 
• 97416-75-6 2-methyl-3-phenylbutanal 
• 1323440-92-1 (Z)-triethyl((2-methyl-3-phenylbut-1-en-1-yl)oxy)silane 

Relevant academic research and scientific papers

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 palladium(II) complexes possessing a tridentate N-heterocyclic carbene amidate alkoxide ligand: Access to oxygen-bridging dimer structures

(Chemical Equation Presented) Catalysts with a bite: Chiral PdII complexes were prepared with tridentate N-heterocyclic carbene amidate alkoxide ligands. Dimeric and monomeric forms were mutually convertible by acid or base treatment (see scheme). The catalysts promote asymmetric Heck reactions efficiently, offering high enantioselectivities far superior to those of existing methods.

Rapid organocatalytic aldehyde-aldehyde condensation reactions

We report the results of the systematic optimization of the α-methylenation of aldehydes with aqueous formaldehyde. A simple combination of a secondary amine catalyst and a weak acid co-catalyst has been identified, allowing access to α-substituted acroleins in a matter of minutes. In the absence of formaldehyde, the catalytic system promoted the self-condensation reaction of α,β-unsaturated aldehydes. Both of these reactions exhibited linear relationships between co-catalyst acidities and reaction rates. A second-order dependence of catalyst concentration was observed, pointing to the involvement of two molecules of the ammonium catalyst in the rate-determining step. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Simple primary anilines as iminium catalysts for the epoxidation of α-substituted acroleins

Simple ortho-alkylated anilines have been shown to be excellent iminium catalysts for the epoxidation reaction of α-substituted acroleins. A range of different α-substituted acroleins give the epoxide products in good to excellent yields and good chemoselectivity.

Mild organocatalytic α-methylenation of aldehydes

A rapid and extremely convenient method for α-methylenation of aldehydes with aqueous formaldehyde is described. Two optimal catalytic systems are presented that allow short reaction times and afford the functionalized products in good to excellent yields (up to 99%) and chemoselectivity.

Stereocontrol in the EtAlCl2-induced cyclization of chiral γ,δ-unsaturated methyl ketones to form cyclopentanones

EtAlCl2-induced cyclization of chiral γ,δ-unsaturated ketones 11c and 17b takes place mainly from the expected face. The selectivity is modest for 11c (60:40) in which the large substituent is a primary alkyl group and the medium substituent is a methyl group and excellent for 17b (93:7) in which the large substituent is a cyclohexyl group and the medium substituent is a methyl group. The cyclization of 17a is anomalous, suggesting that the phenyl group has more than a simple steric effect.