650638-45-2

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 587-04-2 m-Chlorobenzaldehyde 

Downstream Products

• 122047-10-3 (R)-(+)-2-hydroxy-2-(3-chlorophenyl)acetonitrile 
• 169032-01-3 (1R)-2-amino-1-(3-chloro-phenyl)-ethanol hydrochloride 
• 121652-86-6 (R)-2-(3-Chlorophenyl)-2-hydroxyethylamine 

Relevant academic research and scientific papers

Chiral lithium binaphtholate aqua complex as a highly effective asymmetric catalyst for cyanohydrin synthesis

A highly enantioselective cyanohydrin synthesis with aromatic aldehydes using chiral lithium binaphtholate aqua or alcohol complexes has been developed and is a simple and inexpensive catalyst suitable for process chemistry to give gram-scale cyanohydrins

Enantioselective cyanosilylation of aldehydes catalyzed by novel camphor derived Schiff bases-titanium(IV) complexes

Five tridentate Schiff bases have been prepared from (1R,2S,3R,4S)-3-amino- 1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol and salicylaldehydes. X-ray structure investigation revealed differences in their molecular conformation, and their titanium(IV) complexes

Investigation of lewis acid versus lewis base catalysis in asymmetric cyanohydrin synthesis

The asymmetric addition of trimethylsilyl cyanide to aldehydes can be catalysed by Lewis acids and/or Lewis bases, which activate the aldehyde and trimethylsilyl cyanide, respectively. It is not always apparent from the structure of the catalyst whether Lewis acid or Lewis base catalysis predominates. To investigate this in the context of using salen complexes of titanium, vanadium and aluminium as catalysts, a Hammett analysis of asymmetric cyanohydrin synthesis was undertaken. When Lewis acid catalysis is dominant, a significantly positive reaction constant is observed, whereas reactions dominated by Lewis base catalysis give much smaller reaction constants. [{Ti(salen)O}2] was found to show the highest degree of Lewis acid catalysis, whereas two [VO(salen)X] (X = EtOSO3 or NCS) complexes both displayed lower degrees of Lewis acid catalysis. In the case of reactions catalysed by [{Al(salen)}2O] and triphenyl- phosphine oxide, a non-linear Ham- mett plot was observed, which is indicative of a change in mechanism with increasing Lewis base catalysis as the carbonyl compound becomes more electron-deficient. These results suggested that the aluminium complex/tri- phenylphosphine oxide catalyst system should also catalyse the asymmetric addition of trimethylsilyl cyanide to ke- tones and this was found to be the case.

Kinetics and mechanism of vanadium catalysed asymmetric cyanohydrin synthesis in propylene carbonate

Propylene carbonate can be used as a green solvent for the asymmetric synthesis of cyanohydrin trimethylsilyl ethers from aldehydes and trimethylsilyl cyanide catalysed by VO(salen)NCS, though reactions are slower in this solvent than the corresponding re

A bimetallic aluminium(salen) complex for asymmetric cyanohydrin synthesis

In the presence of a phosphine oxide cocatalyst, a bimetallic aluminium(salen) complex was found to catalyse the asymmetric addition of trimethylsilyl cyanide to aldehydes. Under optimised conditions, enantioselectivities of 53-96% were obtained using 2 m

Catalytic, asymmetric cyanohydrin synthesis in propylene carbonate

Propylene carbonate can be used as a green solvent for asymmetric cyanohydrin synthesis catalyzed by VO(salen)NCS. A range of 10 aromatic and aliphatic aldehydes gave high enantioselectivities (up to 93%) and conversions (up to 100%) in reactions carried

[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.

Enantioselective synthesis of cyanohydrins by a novel aluminum catalyst

The development of a new chiral aluminum catalyst is reported. This catalyst has been applied efficiently to the asymmetric cyanosilylation of aldehydes.