Regio- and stereocontrolled synthesis of borylated E-enynes, Z-enediynes and derivatives from alkenyl-1,2-bis-(boronates).

An efficient stereo-controlled synthesis of enyne and enediyne derivatives, via sequential Suzuki-Miyaura coupling reactions from easily prepared 1-alkene-1,2-diboronic esters and alkynyl bromides, is reported. The resulting enyne boronic esters were subjected to Borono-Mannich and Suzuki coupling reactions independently to obtain α,ß-unsaturated aminoester and tri-substituted olefin derivatives, respectively. Additionally, divergent syntheses of triazole and cyclopropylboronate derivatives are also reported.

Supramolecular Chiral Helical Ribbons of Tetraphenylethylene-Appended Naphthalenediimide Controlled by Solvent and Induced by l- and d-Alanine Spacers.

Naphthalenediimide-tetraphenylethylene conjugates with an alanine spacer (coded as: NDI-(Ala-TPE)2 ) were synthesized to study the influence of the chirality of the amino acid spacer on its self-assemblies. Here we particularly show that NDI-Ala-TPE bearing l-alanine gives left-handed (M-type) helical superstructure, while d-alanine produces right-handed (P-type) helical ribbons in THF:H2 O at 40:60 % v/v ratio. However, particular aggregates were observed at 20:80 % v/v ratio. Circular dichroism was used to characterise the induction of chirality and the handedness of the helical superstructures, and the microstructure of the self-assembled materials was visualised using scanning electron microscopy while DLS analysis confirmed the formation of particular aggregates in solution.