Thiete Dioxides as Templates Towards Twisted Scaffolds and Macrocyclic Structures

Abstract

Thiete dioxide units have been employed as a template for further functionalization through C−H activation strategies. Using simple thiete dioxide building blocks, a new library of axially chiral molecules has been synthesized that owe their stability to electrostatic interactions in the solid state. Similar starting materials were further engaged in the formation of cyclic trimeric structures, opening the pathway to unprecedented macrocyclic ring systems.

Uncommon Four‐Membered Building Blocks – Cyclobutenes, Azetines and Thietes

“…Playing with the electron‐donating and ‐withdrawing nature of the substituents allowed for the synthesis of a wide variety of new molecules that could be crystallized as racemates (Figure 2). [67] …”

Skeletal reorganization divergence of N-sulfonyl ynamides

“…Moreover, they could participate in [3 + 2] cycloadditions with diazo compounds or nitrile oxides for the synthesis of heterocycles 23,24 . Recently, thiete sulfones have been investigated in C-H functionalization to establish axially chiral molecules and macrocyclic compounds 25,26 . However, the conventional synthesis of thiete sulfones relies on multi-step routes and also suffers from narrow scope [27][28][29][30][31][32] .…”

Stereoselective Access to Azetidine-Based α-Amino Acids and Applications to Small Peptide Synthesis

“…Following our recent advances on the synthesis of four-membered carbo- and heterocycles, − we set out to investigate the formation of non-natural substituted amino acids through a simple stereocontrolled sequence involving the intermediate formation of unsaturated prochiral azetinyl-carboxylic acids. We envisioned that further asymmetric hydrogenation would furnish the desired functionalized azetidine carboxylic acid compounds diastereo- and enantioselectively (Scheme C) .…”