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

Luo, Yunfei; Roy, Iain D.; Madec, Ama�l G.E.; Lam, Hon Wai

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), https://doi.org/10.1002/anie.201310380

• 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: https://nottingham-repository.worktribe.com/output/725135
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.201310380/abstract
• 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.wiley.com/doi/10.1002/anie.201310380/abstract. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.