1070980-41-4

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 7677-24-9 trimethylsilyl cyanide 
• 645-49-8 cis-stilben 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 117306-12-4 (2R,3E)-2-hydroxy-4-phenyl-3-butenenitrile 

Relevant academic research and scientific papers

Asymmetric trimethylsilylcyanation of aldehydes catalyzed by chiral (salen)Ti(IV) complexes

A set of aromatic, aliphatic and α,β-unsaturated aldehydes has been asymmetrically trimethylsilylcyanated with e.e.'s ranging from 40% to 80% using a chiral (salen)Ti(IV) catalyst prepared in situ from titanium tetraisopropoxide and (1R,2R)-[N,N'-bis(2'-h

Thiourea-catalyzed enantioselective cyanosilylation of ketones

The new chiral amino thiourea catalyst 3d promotes the highly enantioselective cyanosilylation of a wide variety of ketones. The hindered tertiary amine substituent plays a crucial role with regard to both stereoinduction and reactivity, suggesting a coop

Fine modification of salen ligands - Effects on the salen-Ti-catalyzed asymmetric cyanosilylation of aldehydes

New bifunctional N-oxide salen-TiIV complexes and a pyrrolidine salen-TiIV complex in combination with achiral N-oxide were developed and applied to the asymmetric addition of trimethylsilyl cyanide to aldehydes. Notably, both enanti

CYANATION CATALYST AND METHOD FOR PRODUCING OPTICALLY ACTIVE CYANHYDRIN COMPOUND USING THE SAME

The present invention can provide a cyanation catalyst represented by the general formula (I): (in the formula (I), R1 through R4 are each an optionally substituted hydrocarbon group; R1 and R2 and/or R3 and R4 may form an optionally substituted carbon chain ring; R5 through R8 are each a hydrogen atom, or an optionally substituted hydrocarbon group; R5 and R6 and/or R7 and R8 may form an optionally substituted carbon chain ring; R9 and R10 are each a hydrogen atom, or an optionally substituted hydrocarbon group; W, X and Y each represent an optionally substituted binding chain; X and/or Y may be non-existent; M represents a metal or a metal ion; and ligands of M may each be located at any position).

[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).

Synthesis of the bifunctional BINOL ligands and their applications in the asymmetric additions to carbonyl compounds

Efficient one-step syntheses of the bifunctional BINOL and H8BINOL ligands (S)-6 and (S)-8 have been developed from the reaction of BINOL and H8BINOL with morpholinomethanol, respectively. The X-ray analyses of these compounds have revealed their structural similarity and difference. The bifunctional H8BINOL (S)-8 is found to be highly enantioselective for the reaction of diphenylzinc with many aliphatic and aromatic aldehydes and especially is the most enantioselective catalyst for linear aliphatic aldehydes. Unlike other catalysts developed for the diphenylzinc addition which often require the addition of a significant amount of diethylzinc with cooling (or heating) the reaction mixture in order to achieve high enantioselectivity, using (S)-8 needs no additive and gives excellent results at room temperature. (S)-8 in combination with diethylzinc and Ti(OiPr)4 can catalyze the highly enantioselective phenylacetylene addition to aromatic aldehydes. It can also promote the phenylacetylene addition to acetophenone at room temperature though the enantioselectivity is not very high yet. Without using Ti(OiPr)4 and a Lewis base additive, (S)-8 in combination with diethylzinc can catalyze the reaction of methyl propiolate with an aldehyde to form the highly functional γ-hydroxy-α,β-acetylenic esters except that the enantioselectivity is low at this stage. The bifunctional BINOL ligand (S)-6 in combination with Me2AlCl is found to be a highly enantioselective catalyst for the addition of TMSCN to both aromatic and aliphatic aldehydes.

Asymmetric cyanosilylation of aldehydes catalyzed by novel chiral tetraaza-titanium complexes

The asymmetric addition of trimethylsilyl cyanide (TMSCN) to a range of aldehydes was efficiently catalyzed by a novel, easily prepared C 2-symmetric chiral tetraaza-Ti(IV) complex in high yields with up to 92% ee under mild conditions. A negative nonlinear effect between the ee of the ligand and the ee of the product was observed. Georg Thieme Verlag Stuttgart.

Asymmetric cyanohydrin synthesis catalyzed by Al(salen)/triphenylphosphane oxide

Various aldehydes undergo asymmetric trimethylsilylcyanation with (CH 3)3SiCN (TMSCN) in the presence of a chiral Al(salen) complex and Ph3PO as the catalyst. This is a double activation where Al(salen) plays the role of Lewis acd and POPh3 acts as a Lewis base. Various kind of aldehydes were subjected to the enantioselective addition of (CH3)3SiCN at temperatures between -40 °C and -50 °C. Hydrolysis of the adducts gave cyanohydrins with over 90 % yield and 80 % ee in most cases. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Highly enantioselective cyanosilylation of aldehydes catalyzed by novel β-amino alcohol-titanium complexes

The β-amino alcohol 1b-Ti(Oi-Pr)4 complex has been shown to catalyze the enantioselective cyanosilylation of aldehydes efficiently. In the presence of 5 mol % of 1b-Ti(Oi-Pr)4 complex catalyst, the aromatic, conjugated, heteroaromatic, and aliphatic aldehydes were converted to their corresponding trimethylsilyl ethers of cyanohydrins in 90-99% yields with up to 94% ee under mild conditions.

Design of a new bifunctional asymmetric catalyst from carbohydrates: Application to catalytic asymmetric cyanosilylation of aldehydes and acetophenone

A new active Lewis acid-Lewis base bifunctional asymmetric catalyst 7 was developed using carbohydrate as a scaffold and this catalyst was applied to the asymmetric cyanosilylation of aldehydes and acetophenone. The β-Ph group at the 6-position of 7 was found to be important for a high asymmetric induction (up to 80% ee) by bringing the Al and the phosphine oxide at optimum positions for a dual activation of carbonyl compounds and TMSCN. (C) 2000 Elsevier Science Ltd.