Synthesis of Functionalized Spirocyclic Oxetanes through Paterno-Buchi Reactions of Cyclic Ketones and Maleic Acid Derivatives

Weronika Michalska; Nathan Halcovitch; Susannah Coote

doi:10.1039/D2CC06459F

Synthesis of Functionalized Spirocyclic Oxetanes through Paterno-Buchi Reactions of Cyclic Ketones and Maleic Acid Derivatives

Weronika Michalska, Nathan Halcovitch, Susannah Coote

Department of Chemistry

Lancaster University

Research output: Contribution to journal › Article › peer-review

6 Citations (SciVal)

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.

Original language	English
Pages (from-to)	784-787
Number of pages	4
Journal	Chemical communications (Cambridge, England)
Volume	59
Issue number	6
Early online date	20 Dec 2022
DOIs	https://doi.org/10.1039/D2CC06459F
Publication status	Published - 18 Jan 2023

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10.1039/D2CC06459FLicence: CC BY

https://pubs.rsc.org/en/content/articlelanding/2023/CC/D2CC06459FLicence: CC BY

Cite this

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title = "Synthesis of Functionalized Spirocyclic Oxetanes through Paterno-Buchi Reactions of Cyclic Ketones and Maleic Acid Derivatives",

abstract = "A telescoped three-step sequence to functionalised spirocyclic oxetanes is reported, involving Patern{\`o}–B{\"u}chi 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.",

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AU - Michalska, Weronika

AU - Halcovitch, Nathan

AU - Coote, Susannah

PY - 2023/1/18

Y1 - 2023/1/18

N2 - 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.

AB - 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.

U2 - 10.1039/D2CC06459F

DO - 10.1039/D2CC06459F

M3 - Article

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JO - Chemical communications (Cambridge, England)

JF - Chemical communications (Cambridge, England)

IS - 6

ER -

Synthesis of Functionalized Spirocyclic Oxetanes through Paterno-Buchi Reactions of Cyclic Ketones and Maleic Acid Derivatives

Abstract

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