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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 Wai Lam



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.

Journal Article Type Article
Publication Date Apr 14, 2014
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1433-7851
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 53
Issue 16
APA6 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
DOI https://doi.org/10.1002/anie.201310380
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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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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