117306-12-4

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 74-90-8 hydrogen cyanide 
• 67-66-3 chloroform 
• 7677-24-9 trimethylsilyl cyanide 
• 151-50-8 potassium cyanide 
• 645-49-8 cis-stilben 
• 79311-09-4 essigsaeure-<(E)-1-cyano-3-phenyl-2-propenyl>ester 
• 104-55-2 3-phenyl-propenal 
• 143-33-9 sodium cyanide 
• 1070980-41-4 (R)-(E)-4-phenyl-2-trimethylsilyloxy-3-butenenitrile 

Downstream Products

• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 107969-82-4 (2R)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid methyl ester 
• 676477-93-3 (2R)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid ethyl ester 
• 140632-55-9 (R)-(E)-2-hydroxy-4-phenyl-3-butenoic acid 

Relevant academic research and scientific papers

Study on the (R)-oxynitrilase activity of Pouteria sapota

Mamey (Pouteria sapota) defatted meal was used to catalyze the enantioselective addition of HCN to α,β-unsaturated aldehydes. Using a biphasic system of diisopropyl ether and citrate buffer (0.1 M, pH 5.0, 10% v/v), the (R)-cyanohydrins obtained showed go

A Facile Synthesis of Optically Active γ-Cyanoallylic Alcohols Using Asymmetric Hydrocyanation of α,β-Alkenyl Aldehydes Followed by Stereospecific Sigmatroopic Chirality Transfer of the Cyanohydrin Acetates

Optically active γ-cyanoallylic alcohols were synthesised by using asymmetric hydrocyanation of α,β-alkenyl aldehydes catalyzed by peptide-titanium complex to give α-cyanoallylic alcohols (cyanohydrins) with high optical yields followed by palladium compl

Regio- and Stereospecific C- and O-Allylation of Phenols via φ-Allyl Pd Complexes Derived from Allylic Ester Carbonates

Two complementary strategies have been developed for the C- and O-allylation of phenols via a common φ-allyl Pd complex. While O-allylation of phenols by this method is a well-recognized reaction of general utility, the associated para-selective C-allylation reaction is still in its infancy. Cationic φ-allyl Pd intermediates, derived from allylic ester carbonates and palladium(0) catalyst, were found to undergo the Friedel-Crafts-type para-selective C-allylations with nine different phenols. Both C- and O-allylated products were obtained in good to excellent yields following a metal-catalyzed regio- and stereospecific substitutive 1,3-transposition. Conditions were also identified that control access to either allylated product. Finally, a study of the equilibrium established between the two allylation products revealed that the O-allylated compound was the kinetic product and the C-allylated compound the thermodynamic product.

Carving the active site of almond R-HNL for increased enantioselectivity

Structure-guided redesign of the active site of almond (R)-PaHNL5 for increased enantioselectivity resulted in four improved muteins. In particular, mutation V360I gave enhanced conversion rates and enantioselectivities higher than 96% ee for two structur

'Gelozymes' in organic synthesis. (Part 3): Lipase mediated synthesis of enantiomerically pure (R)- and (S)-enantiomers of 2-acetoxy-4-phenyl-(E)-but-3- enenitrile

Lipases such as Candida rugosa lipase and Pseudomonas cepacia (Amano Ps) lipase immobilized in gelatin gels (gelozymes) exhibit very high enantioselectivities (E>200) during alcoholysis of racemic 2-acetoxy-4-phenyl-(E)-but-3-enenitrile with n-butanol in hexane and diisopropyl ether. C. rugosa lipase in n-hexane shows selectivity towards the (R)-ester while P. cepacia (Amano Ps) lipase shows selectivity towards the (S)-ester producing the corresponding cyanohydrins. After decomposition of the cyanohydrin by treatment with 1M imidazole solution to cinnamaldehyde and its removal by bisulfite treatment, (R)- or (S)-enantiomer of 2-acetoxy-4-phenyl-(E) -but-3-enenitrile can be obtained in high yields (90%) and high enantiomeric excess (>99%).

Enantioselective hydrocyanation of aldehydes catalyzed by [Li{Ru(phgly)2(binap)}]X (X = Cl, Br)

Novel bimetallic complexes [Li{Ru[(S)-phgly]2[(S)-binap]}]X (X = Cl, Br) are readily synthesized by mixing Ru[(S)-phgly]2[(S)-binap] and LiX. A single-crystal X-ray analysis reveals the structure. These bimetallic complexes efficient

α-Pinene-type chiral Schiff bases as tridentate ligands in asymmetric addition reactions

A group of tridentate Schiff bases derived from (+)-α-pinene were synthesized. The steric effects in the transition state, the importance of π-π stacking interactions as well as the electronic effects of aryl aldehydes according to Hammett constant values in the enantioselective addition of Et2Zn to aldehydes with the use of Schiff bases as chiral ligands are described. Also, a variety of aldehydes were cyanated using a catalyst prepared in situ from titanium tetraisopropoxide and chiral Schiff bases. The influence of a conjugated double-bond in the cyanation substrates on enantioselectivity was observed. The chemical structures of the chiral Schiff base-titanium alkoxide complexes are discussed based on their 1H and 13C NMR spectra. 3D models of the Zn2-complex catalyst and Ti-complex catalyst containing α-pinane-type Schiff bases based on X-ray diffraction experiments are postulated. The models presented were consistent with the reported chirality of the addition product and observed ee.

Asymmetric synthesis of a new salen type-titanium complex as the catalyst for asymmetric trimethylsilylcyanation of aldehydes

This work describes the asymmetric synthesis of a new salen-type ligand via a Diels-Alder reaction and Curtius rearrangement. The ligand with a norbornane skeleton was used in the trimethylsilylcyanation of aldehydes, but the enantioselectivity was 55%ee. The norborane skeleton was cleaved to destroy this rigidity, and the eanatioselectivity was thereby increased to 85%ee.

[Ru(phgly)2(binap)]/Li2CO3: A Highly Active, Robust, and Enantioselective Catalyst for the Cyanosilylation of Aldehydes

The right combination: A series of aromatic, heteroaromatic, aliphatic, and α,β-unsaturated aldehydes can be converted into the desired silylated cyanohydrins by reaction with (CH3)3SiCN and a catalyst system consisting of the combination of a chiral ruthenium complex and Li2CO3 (see scheme). The reaction is highly enantioselective and affords the R products with up to 98% ee within 24 h at a substrate-tocatalyst ratio of 10000:1. (Chemical Equation Presented).

A novel chiral (salen)AlIII complex catalyzed asymmetric cyanosilylation of aldehydes

A novel chiral (salen)AlIII complex was synthesized through the reaction of Et2AlCl and salen (R,R)-1 derived from (R,R)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene. This complex is an efficient catalyst for the asymmetric trimethylsilylcyanation of aldehydes in the presence of tributylphosphane oxide as an additive. The use of 1 mol-% of the complex led to the corresponding cyanohydrins in high yields (85-94%) with good-to-excellent enantioselectivities (42-92%ee). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.