Aminonitrile formation chiral

Functionalized amines. The LiClO -catalyzed three-component condensation, that result in the formation of a-aminonitriles using chiral amines and aldehydes is... 

The double dynamic system comprised 24 chiral aminonitrile intermediates, carrying different substituents on the aromatic moiety and the /V-position, and was subsequently challenged by the lipase-mediated amidation resolution process. Not only H-XMR spectroscopy was used to follow the reactions HPLC, through the integration of preparative Zorbax and chiral OD-H columns, was used to confirm the product formations and to analyze the enantioselectivities. According to both analyses, the results indicated that only /V-methyl aminonitriles, produced from methylamine A, were transformed by the lipase resolution process. The major product was found to be amide 33A, derived from its corresponding intermediate 32A. The other products were amides 36A and 30A. 

Asyimnetric induction is observed in 2,3-sigmatropic rearrangements via chiral ammrtninm chlorides such as (56), which was obtained from (S)-proline ethyl ester. Ylide formation with potassium r-butox-ide, rearrangement and acid hydrolysis of the aminonitrile affords (/ )-(+)-methyl-2-phenyl-3-butenal (90% optical purity) (equation 28). Application of this sequence furnishes in a new tq)-... 

The Strecker reaction [48], discovered in 1850 [1], is the most practical and efficient tool for the preparation of a-amino acids [49] via the formation of a-aminonitriles (Scheme 10.15) [50]. This three-component coupling between an amine or its equivalent, a carbonyl compound (generally an aldehyde), and hydrogen cyanide or its alkaline metal cyanides can be also made enantioselectively through the use of both metal-based catalysts and chiral organocatalysts. 

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