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

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

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. https://doi.org/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: https://nottingham-repository.worktribe.com/output/754882
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.201502484/abstract
• 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.wiley.com/doi/10.1002/anie.201502484/abstract. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.