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Enantioselective synthesis of allylboronates and allylic alcohols by copper-catalyzed 1,6-boration

Luo, Yunfei; Roy, Iain D.; Madec, Amaël G.E.; Lam, Hon Wai

Authors

Yunfei Luo

Iain D. Roy

Amaël G.E. Madec

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



Abstract

Chiral secondary allylboronates are obtained in high enantioselectivities by the copper-catalyzed 1,6-boration of electron-deficient dienes with B2(pin)2. The reactions proceed efficiently using catalyst loadings as low as 0.0049 mol%. The allylboronates may be oxidized to the allylic alcohols, and can be used in stereoselective aldehyde allylborations. This process was applied to a concise synthesis of atorvastatin.

Citation

Luo, Y., Roy, I. D., Madec, A. G., & Lam, H. W. (2014). Enantioselective synthesis of allylboronates and allylic alcohols by copper-catalyzed 1,6-boration. Angewandte Chemie International Edition, 53(16), doi:10.1002/anie.201310380. ISSN 1433-7851

Journal Article Type Article
Acceptance Date Feb 5, 2014
Online Publication Date Mar 12, 2014
Publication Date Apr 14, 2014
Deposit Date Feb 12, 2016
Publicly Available Date Feb 12, 2016
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1433-7851
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 53
Issue 16
DOI https://doi.org/10.1002/anie.201310380
Public URL http://eprints.nottingham.ac.uk/id/eprint/31656
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201310380/abstract
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc/4.0
Additional Information This is the peer reviewed version of the following article: Luo, Y., Roy, I. D., Madec, A. G. E. and Lam, H. W. (2014), Enantioselective Synthesis of Allylboronates and Allylic Alcohols by Copper-Catalyzed 1,6-Boration. Angew. Chem. Int. Ed., 53: 4186–4190. doi:10.1002/anie.201310380, which has been published in final form at http://onlinelibrary.wi...nie.201310380/abstract. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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HWL Yunfei Iain Amael 1,6-Boration ACIE Submission (accepted).pdf (888 Kb)
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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by-nc/4.0





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