One of the biggest challenges in asymmetric synthesis is to prevent racemization of enantiopure starting materials. However, at least some of the enantiopurity is lost in most of the existing reactions used in synthetic organic chemistry. This translates into unnecessary material losses. Naturally enantiopure proteinogenic amino acids that can be transformed into many useful intermediates in dr...

Isocyanide-based multicomponent reactions (IMCR) are by far the most versatile reactions that can construct relatively complex molecules by one-pot synthesis. More importantly, the development of post IMCR modifications significantly improves the scaffold's diversity. Here, we describe the use of N-Boc protected hydrazine together with α-amino acid derived isocyanides in the Ugi tetrazole react...

The only evidence of vaccine-induced protection from HIV acquisition in humans was obtained in the RV144 HIV vaccine clinical trial. One immune correlate of risk in RV144 was observed to be higher titers of vaccine-induced antibodies (Abs) reacting with a 23-mer non-glycosylated peptide with the same amino acid sequence as a segment in the second variable (V2) loop of the MN strain of HIV. We u...

The unprecedented electrophilic iodo-mediated cyclization of α-amino-ynones afforded enantiomerically enriched β-iodopyrrolin-4-ones in excellent yields under mild conditions. The starting substituted α-amino-ynones were obtained from the chiral pool by selective mono-addition of an organolithium to optically pure N-protected carboxyanhydrides of amino acids (UNCAs).

An enantioselective β-carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N-heterocyclic-carbene-bound α,β-unsaturated acyl azolium intermediate constructs a new carbon-nitrogen bond asymmetrically. The pyrazolidinone products ...

α-amino acids bearing aromatic side chains are important synthetic units in the synthesis of peptides and natural products. Although various β-C-H arylation methodologies for amino acid derivatives involving the assistance of directing groups have been extensively developed, syntheses that directly employ N-protected amino acids as starting materials remain rare. Herein, we report an N-acetylgl...

Two darts in the middle! This work reports double addition of propargylzinc reagents to nitriles (acylcyanohydrins and cyanocarbonates). methodology provides a straightforward access dipropargylic α,α-disubstituted hydroxyamides or N-Boc-protected amino alcohols which can be converted into functionalized pyridine derivatives after cobalt-catalyzed [2+2+2] cycloaddition reactions involving nitri...