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Developing the Scope of O→C Aryl Migrations: Exploring Amide Substrates as Potential Precursors for Asymmetric Reactions

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Ameen, Dana and Snape, Timothy James ORCID: 0000-0003-2766-4491 (2014) Developing the Scope of O→C Aryl Migrations: Exploring Amide Substrates as Potential Precursors for Asymmetric Reactions. European Journal of Organic Chemistry, 2014 (9). pp. 1925-1934. ISSN 1434-193X

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Official URL: http://dx.doi.org/10.1002/ejoc.201301716

Abstract

A new and mild method for the production of diasteromerically enriched α-aryl carbonyl compounds has been achieved. Although only modest diastereoselectivies are observed, they demonstrate the potential of the method for further optimisation. It also appears that reactions that proceed through a five-membered spirocyclic transition state rearrange, whereas those proceeding through a six-membered transition state do not, but stop at the diaryl ether stage.

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