Chain walking of allylrhodium species towards esters during rhodium-catalyzed nucleophilic allylations of imines

Mart�nez, Jose I.; Smith, Joshua S.; Hepburn, Hamish B.; Lam, Hon Wai

Abstract

Allylrhodium species derived from δ-trifluoroboryl β,γ-unsaturated esters undergo chain walking towards the ester moiety.The resulting allylrhodium species react with imines to give products containing two new stereocenters and a Z-alkene. By using a chiral diene ligand, products can be obtained with high enantioselectivities, where a pronounced matched/mismatched effect with the chirality of the allyltrifluoroborate is evident.

Citation

Martínez, J. I., Smith, J. S., Hepburn, H. B., & Lam, H. W. (2016). Chain walking of allylrhodium species towards esters during rhodium-catalyzed nucleophilic allylations of imines. Angewandte Chemie International Edition, 55(3), 1108-1112. https://doi.org/10.1002/anie.201508964

• Journal Article Type: Article
• Online Publication Date: Dec 3, 2015
• Publication Date: Jan 18, 2016
• Deposit Date: Nov 9, 2015
• Publicly Available Date: Sep 25, 2018
• Journal: Angewandte Chemie International Edition
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 55
• Issue: 3
• Pages: 1108-1112
• DOI: https://doi.org/10.1002/anie.201508964
• Public URL: https://nottingham-repository.worktribe.com/output/770310
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.201508964/full
• Contract Date: Sep 25, 2018