Synthesis of functionalized spirocyclic oxetanes through Paternò–Büchi reactions of cyclic ketones and maleic acid derivatives †

Michalska, Weronika Z. and Halcovitch, Nathan R. and Coote, Susannah C. (2022) Synthesis of functionalized spirocyclic oxetanes through Paternò–Büchi reactions of cyclic ketones and maleic acid derivatives †. Chemical Communications. ISSN 1359-7345

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Abstract

A telescoped three-step sequence to functionalised spirocyclic oxetanes is reported, involving Paternò–Büchi reactions between maleic acid derivatives and cyclic ketones. p-Xylene suppresses the competing alkene dimerization that has plagued previous work, allowing access to 35 novel spirocyclic oxetanes that cannot be prepared using existing methodologies, and which represent versatile intermediates for further elaboration.

Item Type:
Journal Article
Journal or Publication Title:
Chemical Communications
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/2500/2504
Subjects:
ID Code:
183080
Deposited By:
Deposited On:
12 Jan 2023 13:50
Refereed?:
Yes
Published?:
Published
Last Modified:
12 Jan 2023 13:50