Catalytic asymmetric transformations of oxa- and azabicyclic alkenes

Abstract

This review provides an overview of the fundamental concepts and recent developments in a wide range of enantioselective transformations involving oxa- and azabicyclic alkenes.

Chiral Bicyclic NHC/Rh Complexes and Their Application to Catalytic Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Amines

“…In transition-metal-catalyzed asymmetric ring-opening reactions, excellent enantioselectivities have been achieved with various chiral phosphine ligands . Although there are more reports on the reactions with chiral phosphine ligands than the reactions with chiral NHC ligands, the same reactions as those with chiral phosphine ligands have been carried out using chiral NHC ligands .…”

Iridium-catalyzed hydroacylation reactions of C1-substituted oxabenzonorbornadienes with salicylaldehyde: an experimental and computational study

“…Transition-metal-catalyzed reactions of strained bicyclic derivatives have been an intense area of research in the last 20 years ( Scheme 1 ) [ 14 – 17 ]. Of particular interest is oxabenzonorbornadiene (OBD, 1 ), as it bears multiple points of reactivity that allow for diverse functionalization.…”

“…Transition-metal-catalyzed reactions of strained bicyclic derivatives have been an intense area of research in the last 20 years (Scheme 1) [14][15][16][17]. Of particular interest is oxabenzonorbornadiene (OBD, 1), as it bears multiple points of reactivity that Scheme 1: Previously reported metal-catalyzed reactions of heterobicyclic alkenes and applications towards the synthesis of biologically active compounds (top).…”

Dual Ni/Organophotoredox Catalyzed Allylative Ring Opening Reaction of Oxabenzonorbornadienes and Analogs

“…The resulting products are also useful building blocks in the synthesis of several classes of biologically active compounds . Our group and many others have extensively studied the transition-metal-catalyzed ring opening reaction and demonstrated that such reactions can be carried out using a broad range of nucleophiles to create new carbon–carbon and carbon–heteroatom bonds …”

“…Numerous carbon-based nucleophiles have been already described for the addition to oxabenzonorbornadienes. These reactions include alkylation with Grignard or zinc reagents, arylation with boronic acids, and cycloadditions . However, less attention has been given to the allylation reaction.…”