These authors contributed equally to this work.
Catalytic Asymmetric Arylation of Enals to Enantioenriched Linear Trisubstituted Allylic Secondary Alcohols by using Aryl Lithiums Generated In Situ from Aryl Bromides
Article first published online: 18 OCT 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Volume 5, Issue 12, pages 3516–3519, December 2013
How to Cite
Zhang, L., Sun, L., Li, Y.-Y., Liu, Y., Yang, Y.-X., Yuan, R., Wang, P. and Da, C.-S. (2013), Catalytic Asymmetric Arylation of Enals to Enantioenriched Linear Trisubstituted Allylic Secondary Alcohols by using Aryl Lithiums Generated In Situ from Aryl Bromides. ChemCatChem, 5: 3516–3519. doi: 10.1002/cctc.201300655
- Issue published online: 27 NOV 2013
- Article first published online: 18 OCT 2013
- Manuscript Received: 6 AUG 2013
- National Natural Science Foundation of China. Grant Number: 21072087
- Program for Changjiang Scholars and Innovative Research Team in University. Grant Number: IRT1137
- asymmetric synthesis;
Catalytic asymmetric addition of nucleophiles to enals is a straightforward method towards enantioenriched allylic alcohols, which are important for the synthesis of natural and pharmaceutically active compounds. Reactive aryl lithiums, produced in situ from readily available and inexpensive aryl bromides and butyl lithium, were used to enantioselectively arylate a number of α-substituted cinnamaldehydes in the presence of tetramethylethylenediamine (TMEDA), AlCl3, and Ti(OiPr)4. This enabled enantioenriched linear trisubstituted allylic secondary alcohols in the catalysis of (S)-H8-BINOL-(TiOiPr)2 complex. TMEDA coordinated the lithium salt generated in situ during transmetallation and effectively inhibited the unwanted background reaction catalyzed by the Lewis acidic lithium salt.