1190935-86-4

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 105090-43-5 N-(thiophen-2-ylmethylene)-1,1-diphenylmethanamine 

Relevant academic research and scientific papers

Oxazoline-based organocatalyst for enantioselective strecker reactions: A protocol for the synthesis of levamisole

A chiral oxazoline-based or-ganocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic N-benzhydrylimines with trime-thylsilyl cyanide (TMSCN) as a cyanide source at -20°C to give α-aminoni-triles in high yield (96%) with excellent chiral induction (up to 98% ee). DFT calculations have been performed to rationalize the enantioselective formation of the product with the organo-catalyst in these reactions. The organo-catalyst has been characterized by single-crystal X-ray diffraction analysis, as well as by other analytical methods. This protocol has been extended to the synthesis of the pharmaceutically important drug molecule levamisole in high yield and with high enantioselectivity.

COMPOUNDS AND RELATED METHODS OF USE

Described herein are compounds of formula (I), related compositions, and their use, for example in the formation of α-amino acids or a precursor thereof such as an α-aminonitrile.

Self-assembled organic-inorganic hybrid silica with ionic liquid framework: A novel support for the catalytic enantioselective Strecker reaction of imines using Yb(OTf)3-pybox catalyst

Yb(OTf)3-pybox is immobilized in a novel self-assembled ionic liquid hybrid silica and has been successfully applied as a catalyst for the asymmetric Strecker hydrocyanation of aldimines. This catalytic system can be reused for at least 6 times without any significant loss of activity and enantioselectivity.

Scaleable catalytic asymmetric Strecker syntheses of unnatural α-amino acids

α-Amino acids are the building blocks of proteins and are widely used as components of medicinally active molecules and chiral catalysts. Efficient chemo-enzymatic methods for the synthesis of enantioenriched α-amino acids have been developed, but it is still a challenge to obtain non-natural amino acids. Alkene hydrogenation is broadly useful for the enantioselective catalytic synthesis of many classes of amino acids, but it is not possible to obtain α-amino acids bearing aryl or quaternary alkyl α-substituents using this method. The Strecker synthesisthe reaction of an imine or imine equivalent with hydrogen cyanide, followed by nitrile hydrolysisis an especially versatile chemical method for the synthesis of racemic α-amino acids. Asymmetric Strecker syntheses using stoichiometric amounts of a chiral reagent have been applied successfully on gram-to-kilogram scales, yielding enantiomerically enriched α-amino acids. In principle, Strecker syntheses employing sub-stoichiometric quantities of a chiral reagent could provide a practical alternative to these approaches, but the reported catalytic asymmetric methods have seen limited use on preparative scales (more than a gram). The limited utility of existing catalytic methods may be due to several important factors, including the relatively complex and precious nature of the catalysts and the requisite use of hazardous cyanide sources. Here we report a new catalytic asymmetric method for the syntheses of highly enantiomerically enriched non-natural amino acids using a simple chiral amido-thiourea catalyst to control the key hydrocyanation step. This catalyst is robust, without sensitive functional groups, so it is compatible with aqueous cyanide salts, which are safer and easier to handle than other cyanide sources; this makes the method adaptable to large-scale synthesis. We have used this new method to obtain enantiopure amino acids that are not readily prepared by enzymatic methods or by chemical hydrogenation.

Catalytic asymmetric Strecker hydrocyanation of imines using Yb(OTf) 3-pybox catalysts

We have explored the highly enantioselective Strecker hydrocyanation of a wide range of aromatic, α,β-unsaturated, heterocyclic, and aliphatic aldimines with good to excellent conversions and ees up to 98% in the presence of catalytic amounts of Yb(OTf)s

Chiral lanthanum(III)-binaphthyldisulfonate complexes for catalytic enantioselective strecker reaction

A catalytic enantioselective Strecker reaction catalyzed by novel chiral lanthanum(III)-binaphthyl disulfonate complexes was developed. The key to promoting the reactions was a semistoichiometric amount of AcOH or i-PrCO2H, which takes advantage of HCN ge