107485-33-6

Upstream product

• 74-90-8 hydrogen cyanide 
• 78-84-2 isobutyraldehyde 
• 151-50-8 potassium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Relevant academic research and scientific papers

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.

Highly active bifunctional salenTi(IV) catalysts for asymmetric cyanosilylation of aldehydes and TMSCN

A novel enantiopure salen ligand bearing a diphenylphosphine oxide on the 3-position of one aromatic ring was synthesized and combined with Ti(Oi-Pr) 4 as a monometallic bifunctional catalyst for asymmetric cyanosilylation reaction of aldehydes with trimethylsilyl cyanide (TMSCN). The catalyst system exhibited excellent activity and moderate enantioselectivity. The addition of TMSCN to 4-nitrobenzaldehyde in the presence of 1 mol% catalyst loading could complete within 10 min at ambient temperature. An intramolecularly cooperative catalysis was observed in this system wherein the central metal Ti(IV) is suggested to play a role of Lewis acid to activate aldehydes while the appended diphenylphosphine oxide worked as Lewis base to activate TMSCN.

Chiral linear polymers bonded alternatively with salen and 1,4-dialkoxybenzene: Synthesis and application for Ti-catalyzed asymmetric TMSCN addition to aldehydes

The synthesis of chiral linear polymers 1a-b having salen and 1,4-dioctyloxybenzene as alternate segments has been accomplished. The GPC analysis showed the molecular weights corresponding to ca. 15 (Mw = 10,999, Mn = 9165 and PDI = 1.20) repeating units for 1a and ca. 8 (Mw = 8547, Mn = 7883 and PDI = 1.08) repeating units for 1b. Polymers 1a-b have been studied with Ti(OiPr)4 as a recyclable catalyst for the asymmetric addition of TMSCN to aldehydes while the selectivity of the polymer catalyst is identical to that of the monomer. The reactions are efficient affording the cyanohydrins with up to 88% ee. The selectivity of the polymer based catalyst 9a is found to be the same to that of the monomer 10a. The reaction provides the advantages of simplified product isolation and easy recovery and recyclability of polymer catalyst 9a without any loss of activity or selectivity.

A new (R)-hydroxynitrile lyase from Prunus mume: Asymmetric synthesis of cyanohydrins

A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC based enantioselective assay technique was developed for the enzyme, which promotes the addition of KCN to benzaldehyde in a buffered solution (pH=4.5).

Highly enantioselective cyanosilylation of aldehydes catalyzed by a Lewis acid-Lewis base bifunctional catalyst

A new bifunctional asymmetric catalyst containing a Lewis acid and a Lewis base (1) was developed and applied to the catalytic asymmetric cyanosilylation of aldehydes. The products were obtained generally with excellent enantiomeric excess. The experiment

Development of a family of β-amino alcohol ligands with two stereocenters for highly efficient enantioselective trimethylsilylcyanation of aldehydes

The asymmetric addition of Me3SiCN to aldehydes catalyzed by titanium(IV) complexes of N-sulfonylated derivatives of β-amino alcohols gave excellent ee's up to 96% ee.

Ueber die erste rekombinante Hydroxynitril-Lyase und ihre Anwendung in der Synthese von (S)-Cyanhydrinen

Keywords: Asymmetrische Synthesen; (S)-Cyanhydrine; Enzymkatalyse; Lyasen

Asymmetric synthesis of tetronic acids by Blaise reaction of protected optically active cyanohydrins

An asymmetric synthesis of tetronic acids is described, involving the Blaise reaction of Reformatsky reagents with silyl-protected optically active cyanohydrins, which were prepared by an enzyme-catalysed method.

Aliphatic (S)-Cyanohydrins by Enzyme Catalyzed Synthesis

The enzyme catalyzed synthesis of aliphatic (S)-cyanohydrins has been accomplished for the first time by application of a hydroxynitrile lyase from leaves of Hevea brasiliensis.The optical purities of (S)-cyanohydrins obtained are in a range between 60 - 97percent.