Bicyclic methylene aziridines and reactions thereof

US9783512B2 · kind B2 · utility

Assignee

• Wisconsin Alumni Research Foundation · US

Inventors

• Jennifer M. Schomaker · Madison, US
• Luke Boralsky · San Francisco, US
• John Hershberger · Plattsburgh, US
• Jared W. Rigoli · Indianapolis, US
• Christopher Adams · Hamburg, DE

Key dates

• Filing date: Nov 13, 2015
• Grant date: Oct 10, 2017
• Expiry date: Nov 13, 2035

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D515/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The oxidative functionalization of olefins is a common method for the formation of vicinal carbon-heteroatom bonds. However, oxidative methods to transform allenes into synthetic motifs containing three contiguous carbon-heteroatom bonds are much less developed. The use of bicyclic methylene aziridines (MAs), prepared via intramolecular allene aziridination, as scaffolds for functionalization of all three allene carbons, among other reactions, is described herein.