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

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Synthesis of functionalized spirocyclic oxetanes through Paternò–Büchi reactions of cyclic ketones and maleic acid derivatives †. / Michalska, Weronika Z.; Halcovitch, Nathan R.; Coote, Susannah C.
In: Chemical Communications, Vol. 59, No. 6, 18.01.2023, p. 784-787.

Research output: Contribution to Journal/MagazineJournal articlepeer-review

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Michalska WZ, Halcovitch NR, Coote SC. Synthesis of functionalized spirocyclic oxetanes through Paternò–Büchi reactions of cyclic ketones and maleic acid derivatives †. Chemical Communications. 2023 Jan 18;59(6):784-787. Epub 2022 Dec 20. doi: 10.1039/d2cc06459f

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@article{4715a1a4fdb0403c8997332ceb34b8f1,
title = "Synthesis of functionalized spirocyclic oxetanes through Patern{\`o}–B{\"u}chi 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.",
author = "Michalska, {Weronika Z.} and Halcovitch, {Nathan R.} and Coote, {Susannah C.}",
year = "2023",
month = jan,
day = "18",
doi = "10.1039/d2cc06459f",
language = "English",
volume = "59",
pages = "784--787",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "6",

}

RIS

TY - JOUR

T1 - Synthesis of functionalized spirocyclic oxetanes through Paternò–Büchi reactions of cyclic ketones and maleic acid derivatives †

AU - Michalska, Weronika Z.

AU - Halcovitch, Nathan R.

AU - Coote, Susannah C.

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 - Journal article

VL - 59

SP - 784

EP - 787

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 6

ER -