Thiete Dioxides as Templates Towards Twisted Scaffolds and Macrocyclic Structures.

Andreas N Baumann,Oliver Trapp,Alexander F Siegle,Peter Mayer,Felix Reiners,Dorian Didier

doi:10.1002/chem.201905751

Andreas N Baumann, Oliver Trapp + Show 4 more

Open Access

https://doi.org/10.1002/chem.201905751

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Journal: Chemistry	Publication Date: Apr 28, 2020
Citations: 6	License type: CC BY 4.0

Affiliation: Ludwig-Maximilians-Universität München

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.

Highlights

Thiete dioxides possess unique electronic and structural properties.[1]
While the first one relies on an a-lithiation/transmetalation/Negishi cross-coupling sequence, the second is based on CÀH activation strategy and allows for a broad and tolerant functionalization of the unsaturated S-containing four-membered ring scaffold
We describe the study of palladium-catalyzed CÀH functionalization of 3substituted thiete dioxides towards the formation of chiral disubstituted thiete dioxides and thiete dioxide-based macrocy

Summary

Introduction

Thiete dioxides possess unique electronic and structural properties.[1]. natural products containing thiete cores were not to be found in the literature, they constitute an interesting entry point to their saturated analogs, thietanes, which have found applications in drug discovery or demonstrated their interesting properties in life-science as pesticide or sweetener.[2]. While the first one relies on an a-lithiation/transmetalation/Negishi cross-coupling sequence, the second is based on CÀH activation strategy and allows for a broad and tolerant functionalization of the unsaturated S-containing four-membered ring scaffold. Given that such structures constitute a unique entry in the repertoire of strained heterocycles, we set out to take the step in their architectural diversification. Thiete dioxide units as a common template for accessing axially chiral disubstituted structures and macrocyclic analogues to the known spherand, first reported by Cram.

Results and Discussion

Conclusions

Conflict of interest