We thank the Netherlands Organization for Scientific Research (NWO-CW) and the National Research School Catalysis (NRSC-C) for financial support. M. P. thanks the Xunta de Galicia for an Angeles Alvariño contract and Fondo Social Europeo.
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Communication
Enantioselective Synthesis of Tertiary and Quaternary Stereogenic Centers: Copper/Phosphoramidite-Catalyzed Allylic Alkylation with Organolithium Reagents†
Article first published online: 19 JAN 2012
DOI: 10.1002/anie.201107840
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Fañanás-Mastral, M., Pérez, M., Bos, P. H., Rudolph, A., Harutyunyan, S. R. and Feringa, B. L. (2012), Enantioselective Synthesis of Tertiary and Quaternary Stereogenic Centers: Copper/Phosphoramidite-Catalyzed Allylic Alkylation with Organolithium Reagents. Angew. Chem. Int. Ed., 51: 1922–1925. doi: 10.1002/anie.201107840
- †
Publication History
- Issue published online: 14 FEB 2012
- Article first published online: 19 JAN 2012
- Manuscript Revised: 9 DEC 2011
- Manuscript Received: 7 NOV 2011
Funded by
- Netherlands Organization for Scientific Research (NWO-CW)
- National Research School Catalysis (NRSC-C)
- Xunta de Galicia
Keywords:
- allylic compounds;
- copper;
- ligand effects;
- organolithium reagents;
- synthetic methods
An efficient and highly enantioselective copper-catalyzed allylic alkylation of disubstituted allyl halides with primary and secondary organolithium reagents using phosphoramidite ligands is reported. The use of trisubstituted allyl bromides allows, for the first time, the enantioselective synthesis of all-carbon quaternary stereogenic centers with these reactive organometallic reagents.