We acknowledge the University of Birmingham for support of M.R.P. The NMR and GC instruments used in this research were obtained through Birmingham Science City: Innovative Uses for Advanced Materials in the Modern World (West Midlands Centre for Advanced Materials Project 2), with support from Advantage West Midlands (AWM) and part funded by the European Regional Development Fund (ERDF). We would also like to thank Graham Burns and Chi Tsang of the School of Chemistry for assistance with HPLC and GC.
Chiral Bases as Useful Probes of Lithium Amide Reactivity†
Article first published online: 24 OCT 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 48, pages 12068–12071, November 26, 2012
How to Cite
Prestly, M. R. and Simpkins, N. S. (2012), Chiral Bases as Useful Probes of Lithium Amide Reactivity . Angew. Chem. Int. Ed., 51: 12068–12071. doi: 10.1002/anie.201206558
- Issue published online: 21 NOV 2012
- Article first published online: 24 OCT 2012
- Manuscript Received: 14 AUG 2012
- University of Birmingham
- lithium amide
Experiments involving competition between chiral and achiral lithium amides provide a qualitative impression of the kinetics of different amide motifs in enolization reactions. The level of enantioselectivity was not diminished by the inclusion of lithium diisopropylamide (LDA; see scheme) into asymmetric enolizations mediated by a chiral lithium amide base, derived from a 1,2-diamine.