Developing a Catalytic Asymmetric Wittig Rearrangement of 2-Benzyloxybenzamides to Chiral Phthalides and Related Products

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The formation and [1,2]-Wittig rearrangement of aryl benzyl ethers provides a convenient method for overall C-C bond formation via the much easier C-O bond formation. Although the reaction is well known, in the absence of a stabilising group it requires harsh conditions and is low yielding so has not been used much in synthesis. A new stereogenic centre is created in the process and where the aryl component bears an ortho-directing group, this not only allows the reaction to proceed in higher yield under milder conditions, but it can be used to influence the stereochemical outcome. This project will now involve detailed development and optimisation towards the corresponding catalytic asymmetric process.