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Stereoselective synthesis of highly substituted tetrahydrofurans by diverted carbene O–H insertion reaction

Nicolle, Simon M.; Lewis, William; Hayes, Christopher J.; Moody, Christopher J.

Authors

Simon M. Nicolle

William Lewis

CHRIS HAYES chris.hayes@nottingham.ac.uk
Professor of Organic Chemistry

Christopher J. Moody



Abstract

Copper or rhodium catalyzed reaction of diazocarbonyl compounds with β-hydroxyketones gives highly substituted tetrahydrofurans with excellent diastereoselectivity, under mild conditions, in a single step process that starts as a carbene O–H insertion reaction but is diverted by an intramolecular aldol reaction.

Citation

Nicolle, S. M., Lewis, W., Hayes, C. J., & Moody, C. J. (2015). Stereoselective synthesis of highly substituted tetrahydrofurans by diverted carbene O–H insertion reaction. Angewandte Chemie International Edition, 54(29), 8485-8489. doi:10.1002/anie.201502484

Journal Article Type Article
Acceptance Date May 7, 2015
Publication Date Jun 9, 2015
Deposit Date Jul 15, 2016
Publicly Available Date Jul 15, 2016
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1521-3773
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 54
Issue 29
Pages 8485-8489
DOI https://doi.org/10.1002/anie.201502484
Public URL http://eprints.nottingham.ac.uk/id/eprint/34963
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201502484/abstract
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
Additional Information "This is the peer reviewed version of the following article: Nicolle, S. M., Lewis, W., Hayes, C. J. and Moody, C. J. (2015), Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene O[BOND]H Insertion Reaction. Angew. Chem. Int. Ed., 54: 8485–8489, which has been published in final form at http://onlinelibrary.wi...nie.201502484/abstract. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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