Affiliation:
1. Department of Chemistry Indiana University 800 E. Kirkwood Ave. Bloomington IN 47401 USA
2. SpiroChem AG, Rosental area, WRO-1047-3 Mattenstrasse 22 4058 Basel Switzerland
Abstract
AbstractRigid bicycles are becoming more popular in the pharmaceutical industry because they allow for expansion to new and unique chemical spaces. This work describes a new strategy to construct 2‐azanorbornanes, which can act as rigid piperidine/pyrrolidine scaffolds with well‐defined exit vectors. To achieve the synthesis of 2‐azanorbornanes, new strain‐release reagent, azahousane, is introduced along with its photosensitized strain‐release formal cycloaddition with alkenes. Furthermore, new reactivity between a housane and an imine is disclosed. Both strategies lead to various substituted 2‐azanorbornanes with good selectivities.
Funder
National Institute of General Medical Sciences
Division of Chemistry
Subject
General Chemistry,Catalysis