A5030431649- Chemical Synthesis and Analysis
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Asymmetric Synthesis and Catalysis
- Synthesis and Catalytic Reactions
- Carbohydrate Chemistry and Synthesis
- Chemical Synthesis and Reactions
- Click Chemistry and Applications
- Glycosylation and Glycoproteins Research
- Supramolecular Self-Assembly in Materials
Universidad de La Rioja
2016-2020
A second generation of chiral bicyclic dehydroalanines easily accessible from serine has been developed. These scaffolds behaved as excellent S-Michael acceptors when tri-O-acetyl-2-acetamido-2-deoxy-1-thio-α-d-galactopyranose (abbreviated GalNAc-α-SH) was used a nucleophile. This addition proceeds with total chemo- and stereoselectivity, complete atom economy, quickly, at room temperature, making it true click reaction. The Michael adducts were transformed into...
A series of fluorescent d-cysteines (Cys) has been synthesized and their optical properties were studied. The key synthetic step is the highly diastereoselective 1,4-conjugate addition aryl thiols to a chiral bicyclic dehydroalanine recently developed by our group. This reaction fast at room temperature proceeds with total chemo- stereoselectivity. Michael adducts easily transformed into corresponding amino acids study and, in some selected cases, N-Fmoc-d-cysteine derivatives be used...
The highly diastereoselective 1,4-conjugate additions of several nitrogen nucleophiles to chiral bicyclic dehydroalanines have been assessed effectively at room temperature in good excellent yields without needing any catalyst or additional base. This methodology is general, simple, oxygen and moisture tolerant, high-yielding, totally chemo- stereoselective. procedure offers an efficient practical approach for the synthesis Nβ-substituted α,β-diamino acids, such as 1-isohistidine,...
Abstract The chiral bicyclic dehydroalanine building block (I) is applied in stereoselective S‐Michael reactions with a variety of thiols.