Carbon-Heteroatom Bond Formation by Rh-Catalyzed Ring-Opening Reactions

Carbon-Heteroatom Bond Formation by Rh -Catalyzed Ring-Opening Reactions [Pg.411]

Since the seminal report by Hogeveen and Middelkoop, our group and others have examined the synthetic utility and mechanistic pathway of the Rh -catalyzed ring-opening of strained bridged bicyclic allylic ethers and amines by heteroatom [Pg.411]

Ring-Opening meso-Oxabicyclic Alkenes with Oxygen-Based Nucleophiles [Pg.412]

based on the arene chromium tricarbonyl scaffold, can also be applied to the Rh -catalyzed ARO reaction, generating the products in high enantioselectivity, albeit in lower yield [8]. [Pg.414]

As more acidic oxygen nucleophiles added preferentially to 7, it was reasoned that carboxylic acids would be good candidates for the ring-opening oxabicyclic alkenes to form the corresponding allylic esters. While certain transition metals, most notably palladium, are known to react with allylic esters to form Jt-allyl intermediates, rhodium-phosphine complexes are less reactive [11]. The product allylic ester formed [Pg.415]