# Chemoselective Aza-Michael Addition of Enolizable Heterocyclic Imine-Thiols to Levoglucosenone

## TL;DR

A new chemical reaction was discovered where certain sulfur and nitrogen compounds react with levoglucosenone to form specific products without forming expected byproducts.

## Contribution

A novel chemoselective aza-Michael addition reaction involving enolizable heterocyclic imine-thiols and levoglucosenone is reported.

## Key findings

- Only aza-Michael addition products were formed, with no S-adducts detected.
- All products were crystalline and obtained in good to excellent yields.
- Product structures were confirmed using NMR, MS, and single-crystal X-ray analysis.

## Abstract

Heterocyclic sulfur and nitrogen containing compounds capable of forming an equilibrium: thiol/imine = thione/amine (N=C-S-H ⇌ H-N-C=S) were reacted with levoglucosenone (LG) in the presence of triethylamine. Unexpectedly, the only isolated products were the result of the aza-Michael addition. No S-adducts were detected. All products were crystalline with good to excellent yields. The structure of products was determined using NMR, MS, and single-crystal X-ray analysis.