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

Martínez, Jose I.; Smith, Joshua S.; Hepburn, Hamish B.; Lam, Hon Wai

Authors

Jose I. Martínez

Joshua S. Smith

Hamish B. Hepburn

HON LAM Hon.Lam@nottingham.ac.uk
Professor of Sustainable Chemistry



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 1433-7851
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 55
Issue 3
Pages 1108-1112
DOI https://doi.org/10.1002/anie.201508964
Public URL http://eprints.nottingham.ac.uk/id/eprint/30669
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201508964/full
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0

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