Divergent Pd-catalyzed cross-coupling of allenyloxazolidinones to give chiral 1,3-dienes and vinyloxazolidinones

Ronald W. Brown; Farzad Zamani; Michael G. Gardiner; Haibo Yu; Stephen G. Pyne; Christopher J. T. Hyland

doi:10.1039/C9SC03215K

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Divergent Pd-catalyzed cross-coupling of allenyloxazolidinones to give chiral 1,3-dienes and vinyloxazolidinones†

Ronald W. Brown,

^a Farzad Zamani,^a Michael G. Gardiner,

^b Haibo Yu,

^a Stephen G. Pyne

^a and Christopher J. T. Hyland

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry and Molecular Bioscience, Molecular Horizons Research Institute, University of Wollongong, Wollongong 2522, NSW, Australia
E-mail: chrhyl@uow.edu.au

^b Research School of Chemistry, Australian National University, Canberra 2601, Australia
E-mail: michael.gardiner@anu.edu.au

Abstract

The divergent reactivity of 5-allenyloxazolidinones has been explored. This novel building block undergoes Pd(0)-catalyzed cross-coupling with boronic acids to form a wide range of chiral 1,3-dienes and pharmaceutically useful vinyloxazolidinones, the chemoselectivity being tightly controlled by a simple switch in additive.

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DOI: https://doi.org/10.1039/C9SC03215K
Article type: Edge Article
Submitted: 01 Jul 2019
Accepted: 03 Aug 2019
First published: 09 Aug 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2019,10, 9051-9056

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Divergent Pd-catalyzed cross-coupling of allenyloxazolidinones to give chiral 1,3-dienes and vinyloxazolidinones

R. W. Brown, F. Zamani, M. G. Gardiner, H. Yu, S. G. Pyne and C. J. T. Hyland, Chem. Sci., 2019, 10, 9051 DOI: 10.1039/C9SC03215K

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Chemical Science

Divergent Pd-catalyzed cross-coupling of allenyloxazolidinones to give chiral 1,3-dienes and vinyloxazolidinones†

Abstract

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Divergent Pd-catalyzed cross-coupling of allenyloxazolidinones to give chiral 1,3-dienes and vinyloxazolidinones

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