Rh^I‐Catalyzed Cycloisomerization of Vinyl Bicyclopropyl Compounds to Azabicyclo[3.2.2]nona‐2,8‐dienes

Abstract

Important class: Nitrogen‐containing heterobicycles are an important structural motif ubiquitous in natural alkaloids. We found that azabicyclo[3.2.2]nona‐2,8‐dienes can be synthesized from vinyl bicyclopropropyl derivatives in the presence of a RhI catalyst (see scheme). Syntheses of such compounds and an investigation into the reaction mechanism through DFT calculations are presented.

Enantioselective One‐pot Synthesis of 3‐Azabicyclo[3.1.0]hexanes via Allylic Substitution and Oxidative Cyclization

“…According to the literature procedure for a synthesis of 2′′ , propargyl amine ( 2’ ) in DCM (1 M) solution was cooled to 0 °C. The sulfonyl chloride 2 ′dh (1.1 equiv.)…”