Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration

Luo, Yunfei; Wales, Steven M.; Korkis, Stamatis E.; Roy, Iain D.; Lewis, William; Lam, Hon Wai

Abstract

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The enantioselective Cu-catalyzed 1,6-boration of (E,E)-α,β,γ,δ-unsaturated ketones is described, which gives homoallylic boronates with high enantiomeric purity and unexpectedly high Z-selectivity. By changing the solvent, the outcome can be altered to give E-allylic boronates.

Citation

Luo, Y., Wales, S. M., Korkis, S. E., Roy, I. D., Lewis, W., & Lam, H. W. (2018). Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration. Chemistry - A European Journal, 24(33), 8315-8319. https://doi.org/10.1002/chem.201801804

• Journal Article Type: Article
• Acceptance Date: Apr 16, 2018
• Online Publication Date: Apr 17, 2018
• Publication Date: Jun 12, 2018
• Deposit Date: Apr 20, 2018
• Publicly Available Date: Apr 20, 2018
• Journal: Chemistry - A European Journal
• Print ISSN: 0947-6539
• Electronic ISSN: 1521-3765
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 24
• Issue: 33
• Pages: 8315-8319
• DOI: https://doi.org/10.1002/chem.201801804
• Keywords: 1,6-addition; asymmetric catalysis; boron; copper; enantioselectivity
• Public URL: https://nottingham-repository.worktribe.com/output/938091
• Publisher URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201801804
• Contract Date: Apr 20, 2018