Design and Mechanistic Insights into α-Helical -Terphenyl Guanidines as Potent Small-Molecule Antifreeze Agents.

Ice formation is a critical challenge across multiple fields, from industrial applications to biological preservation. Inspired by natural antifreeze proteins, we designed and synthesized a new class of small-molecule antifreezes based on α-helical -terphenyl scaffolds with guanidine side chains. These -terphenyl guanidines , among the smallest molecules that mimic α-helical structures, exhibit potent ice recrystallization inhibition (IRI) activity, similar to that of existing large α-helical antifreeze compounds.

Application of 2-Azabicyclo[2.2.1]Hept-5-En-3-One (Vince Lactam) in Synthetic Organic and Medicinal Chemistry.

2-Azabicyclo[2.2.1]hept-5-en-3-one (Vince lactam) is known to be a valuable building block in synthetic organic chemistry and drug research.

Alkylation and silylation of α-fluorobenzyl anion intermediates.

Simple α-fluorobenzyl anions reacted with electrophiles such as non-activated alkyl halides and chlorotrimethylsilane. Upon treatment with LTMP as the base, fluoromethylbenzenes took part in the formation of α-monofluorobenzyl anions without stabilizing -substituents. Furthermore, the resulting α-silyl fluoromethylbenzenes reacted with electrophiles such as acetophenone and benzaldehyde in the presence of cesium fluoride to form α-fluorobenzylated alcohols.

Application of Metathesis Protocols to the Stereocontrolled Synthesis of some Functionalized β-Amino Esters and Azaheterocycles.

In this account our aim was to give an insight into the application of metathesis protocols (ROM, RCM, RCEYM, CM, RRM) for the synthesis of various azaheterocyclic frameworks. Due to the high biological potential and importance in peptide chemistry and drug design of β-amino acids our intention is to give a highlight on the synthetic procedures and transformation of these class of compounds with the above-mentioned metathesis strategies with emphasis on selectivity, stereocontrol, substrate-directing effect or functional group tolerance.

Fluorinated Imines in Tandem and Cycloaddition Reactions.

The chemistry of fluorinated compounds has experienced extraordinary growth in recent decades due to the many and varied properties which many of the compounds that contain fluorinated groups possess. Among all of them, fluorinated chiral imines, in particular the Ellman's imines, are of great importance since they are some of the most interesting building blocks for the synthesis of a large number of enantioenriched carbocycles and heterocycles with extraordinary biological and synthetic properties. This personal account covers the most significant results obtained in our research group in the last two decades concerning asymmetric tandem reactions, paying special attention to the intramolecular aza-Michael reaction (IMAMR), diversity oriented synthesis (DOS), asymmetric tandem reactions involving a p-tolylsulfinyl group as chiral inducer and cycloaddition processes, in particular, the Pauson-Khand reaction, [2+2+2]-cycloadditions and metathesis reactions, starting mainly from enyne compounds and through the use of fluorinated chiral N-sulfinyl imines and their derivatives as starting materials.