In this work, we describe the one-pot synthesis of α-amino nitrile units by concomitant addition alkyl (or aryl) Grignard reagents and TMS cyanide through alkylative Strecker cyanation from readily available formamides. The reaction is broad in scope conditions are mild, inexpensive, easy to set-up, providing numerous nitriles good yields (34 examples, 41–94 % yield).

The Strecker reaction of acetaldehyde, NH3, and HCN to afford alanine was studied by DFT calculations for the first time, which involves two reaction stages. In the first reaction stage, the aminonitrile was formed. The rate-determining step is the deprotonation of the NH3 (+) group in MeCH(OH)-NH3 (+) to form 1-aminoethanol, which occurs with an activation energy barrier (ΔE (≠)) of 9.6 kcal/m...

BACKGROUND The classical Strecker reaction is one of the simplest and most economical methods for the synthesis of racemic α-aminonitriles (precursor of α-amino acids) and pharmacologically useful compounds. RESULTS Indium powder in water is shown to act as a very efficient catalyst for one-pot, three-component synthesis of α-aminonitriles from diverse amines, aldehydes and TMSCN. This genera...

The enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones is presented. Using trimethylsilyl cyanide (TMSCN) as the cyanide source, the reaction can be efficiently catalyzed by a tert-leucine-derived bifunctional thiourea to afford the corresponding hydrazino nitriles in good to excellent yields (50-96%) and moderate to good enantioselectivities, up to 86% e...

Many reports can be obtained on the mechanism for the Maillard reaction between amino acids and reducing sugars. Most of these reports have concentrated on the early stage of this reaction, including the formation of N-glucosides, Amadori rearrangement and the decomposition of Amadori compounds.i) In consequence, various intermediates have been identified, whose roles in the advanced stage of t...

Recently it has been demonstrated that the typical aroma of oxidative spoiled white wine are related with the presence of methional and phenylacetaldehyde, substances accountable respectively for the “boiled-potato” and “honey-like” odour notes with threshold values of 0.5 μg/L and 25 μg/L . These compounds can be formed by the direct oxidation of the respective alcohol or via Strecker degradat...

A camphor-derived sulfonimine with a conjugated carbonyl group, oxoimine 1 (O2SNC10H13O), reacts with amino acids (glycine, L-alanine, L-phenylalanine, L-leucine) to form a compound O2SNC10H13NC10H14NSO2 (2) which was characterized by spectroscopic means (MS and NMR) and supported by DFT calculations. The product, a single diastereoisomer, contains two oxoimine units connected by a -N= bridge, ...

Many reports can be obtained on the mechanism for the Maillard reaction between amino acids and reducing sugars. Most of these reports have concentrated on the early stage of this reaction, including the formation of N-glucosides, Amadori rearrangement and the decomposition of Amadori compounds.i) In consequence, various intermediates have been identified, whose roles in the advanced stage of t...