Acid-Catalyzed Oxy-aminomethylation of Styrenes

We report a strong Brønsted acid-catalyzed three-component oxy-aminomethylation of styrenes with sym-trioxane and sulfonamides or carbamates. This transformation provides a variety of 1,3-oxazinanes in moderate to good yields under mild reaction conditions. The obtained heterocycles can be readily t...

Full description

Saved in:
Bibliographic Details
Published in:ACS catalysis 2024-01, Vol.14 (2), p.751-756
Main Authors: Guillén, Marian, Liu, Sensheng, Díaz-Oviedo, C. David, Klussmann, Martin, List, Benjamin
Format: Article
Language:English
Subjects:
Letter
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We report a strong Brønsted acid-catalyzed three-component oxy-aminomethylation of styrenes with sym-trioxane and sulfonamides or carbamates. This transformation provides a variety of 1,3-oxazinanes in moderate to good yields under mild reaction conditions. The obtained heterocycles can be readily transformed into the corresponding 1,3-amino alcohols, which are useful building blocks for the synthesis of pharmaceutically relevant molecules. Mechanistic studies suggest the intermediacy of an in situ formed 1,3,5-dioxazinane and a subsequent reaction with the olefin.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.3c05342