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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.

Journal Article Type Article
Publication Date Jun 9, 2015
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
APA6 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
DOI https://doi.org/10.1002/anie.201502484
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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