A Dienyl Boronate‐Aryl Nitroso Ene Reaction Entry to C‐Pyrrolyl Nitrones and Subsequent Conversion to Isoxazolidines

Eberlin, L.; Macé, A.; Batsanov, A.S.; Carboni, B.; Whiting, A.

doi:10.1002/slct.201800945

A Dienyl Boronate‐Aryl Nitroso Ene Reaction Entry to C‐Pyrrolyl Nitrones and Subsequent Conversion to Isoxazolidines

Eberlin, L.; Macé, A.; Batsanov, A.S.; Carboni, B.; Whiting, A.

Authors

L. Eberlin

A. Macé

A.S. Batsanov

B. Carboni

Professor Andrew Whiting andy.whiting@durham.ac.uk
Emeritus Professor

Abstract

A new cascade reaction to access C‐pyrrolyl nitrones en route to isoxazolidines is reported; a process that involves four successive steps, the first key step being an ene‐reaction of a 3‐methyl‐1,3‐dienylboronate ester with an aryl nitroso compounds to derive uncommon 1,3‐dipoles which react with various alkenes to access isoxazolidines. The scope and mechanism of the cascade sequence is discussed.

Citation

Eberlin, L., Macé, A., Batsanov, A., Carboni, B., & Whiting, A. (2018). A Dienyl Boronate‐Aryl Nitroso Ene Reaction Entry to C‐Pyrrolyl Nitrones and Subsequent Conversion to Isoxazolidines. ChemistrySelect, 3(16), 4557-4561. https://doi.org/10.1002/slct.201800945

Journal Article Type	Article
Acceptance Date	Apr 26, 2018
Online Publication Date	Apr 25, 2018
Publication Date	Apr 30, 2018
Deposit Date	Apr 27, 2018
Publicly Available Date	Apr 25, 2019
Journal	ChemistrySelect
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	3
Issue	16
Pages	4557-4561
DOI	https://doi.org/10.1002/slct.201800945

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Copyright Statement
This is the peer reviewed version of the following article: Eberlin, L., Macé, A., Batsanov, A. S., Carboni, B. & Whiting, A. (2018). A Dienyl Boronate‐Aryl Nitroso Ene Reaction Entry to C‐Pyrrolyl Nitrones and Subsequent Conversion to Isoxazolidines. ChemistrySelect 3(16): 4557-4561, which has been published in final form at https://doi.org/10.1002/slct.201800945. This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for self-archiving.