A novel, three-component C-C, C-N and C-O bond forming reaction is described. In the presence of 20 mol% CuO, this condensation reaction of CF3CHN2, nitriles, and aldehydes proceeds to afford CF3-substituted oxazolines in moderate to high yields with excellent diastereoselectivities. Subsequent ring-opening of oxazolines gives rise to the corresponding vicinal amino alcohols.

Difunctionalization of alkenes has become a powerful tool for quickly increasing molecular complexity in synthesis. Despite significant progress in the area of alkene difunctionalization involving the incorporation of a nitrogen atom across the C-C double bonds, approaches for the direct 1,2-carboamination of alkenes to produce linear N-containing molecules are scarce and remain a formidable ch...

The one-step conversion of aliphatic carboxylic acids to the corresponding nitriles has been accomplished via the merger of visible light mediated photoredox and cyanobenziodoxolones (CBX) reagents. The reaction proceeded in high yields with natural and non-natural α-amino and α-oxy acids, affording a broad scope of nitriles with excellent tolerance of the substituents in the α position. The di...

Isothiocyanates are the most intensively studied breakdown products of glucosinolates from Brassica plants and well recognized for their pleiotropic effects against cancer but also for their genotoxic potential. However, knowledge about the bioactivity of glucosinolate-borne nitriles in foods is very poor. As determined by GC-MS, broccoli glucosinolates mainly degrade to nitriles as breakdown p...

An efficient methodology to oxidize benzylic and cinnamyl alcohols to their corresponding nitriles in excellent yields has been developed. This methodology employs DDQ as an oxidant and TMSN(3) as a source of nitrogen in the presence of a catalytic amount of Cu(ClO(4))(2)·6H(2)O.

Novel routes for the preparation of 2-amino-4H-pyran-3-carbonitrile 9, amino-arylbenzoic acid ester derivatives 13a,b, 2-aminotetrahydro-4H-chromene-3-carbonitrile 18, 3-amino-4-cyanotetrahydronaphthalene-2-carboxylic acid ester 26 and 4-amino-3,5-dicyanophthalic acid ester derivatives 37a-c were developed. The synthetic methods utilize one-pot reactions of acetylene carboxylic acid esters, α,β...

3.1. Overview 2807 3.2. Chiral Aluminum(III) Complexes as a Catalyst 2808 3.2.1. Aluminum(III)-Salen-Based Catalysts 2808 3.2.2. Aluminum(III)-Binaphthol-Based Catalysts 2810 3.3. Chiral Titanium(IV) Complexes as a Catalyst 2814 3.3.1. Titanium(IV)-Peptide-Based Catalysts 2814 3.3.2. Titanium(IV)-Diol-Based Catalysts 2817 3.4. Chiral Zirconium(IV) Complexes as a Catalyst 2818 3.4.1. The Catalyt...

Next-generation DNA sequencing (NGS) has made it feasible to sequence large number of microbial genomes and advancements in computational biology have opened enormous opportunities to mine genome sequence data for novel genes and enzymes or their sources. In the present communication in silico mining of microbial genomes has been carried out to find novel sources of nitrilases. The sequences se...

In previous papers from this laboratory (1, 2) it has been reported that a-amino acids undergo a quantitative decarboxylation.in aqueous solution when treated with N-bromosuccinimide. Under the conditions used\ (a temperature of 30” and a pH of 3 to 5), the reaction was complete in 30 minutes. Anomalies in behavior were observed with glycine and /3-alanine. The consumption of N-bromosuccinimide...