Mild, calcium catalysed Beckmann rearrangements

McLaughlin, M, Kiely-Collins, H, Brennan, P and Sechi, I (2018) Mild, calcium catalysed Beckmann rearrangements. Chemical Communications, 54 (6). pp. 654-657. ISSN 1359-7345

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Abstract

A mild calcium catalysed Beckmann rearrangement has been realised, which forgoes the more traditional harsh reactions conditions associated with the transformation. The catalyst system is shown to be tolerant towards a wide variety of func-tional groups relevant to natural product synthesis and medicinal chemistry and the synthetic utility of the reaction has also been investigated. A preliminary mechanistic investigation was performed to understand the nature of the incoming nucleophile and a possible reaction pathway is described.