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A series of chiral secondary amines, incorporating a 5- or 6-membered heterocycle, were synthesised and used to prepare novel chiral magnesium bisamide reagents. These amide bases were subsequently applied within asymmetric deprotonation reactions to probe the potential for chelation-assisted selectivity enhancement. Good levels of selectivity could be achieved (up to 87:13 e.r. (R:S)) across a range of prochiral cyclohexanone substrates when employing a thiophene-derived magnesium bisamide complex.
- asymmetric synthesis
Kerr, W., Middleditch, M., & Watson, A. (2011). New potentially chelating chiral magnesium amide bases for use in enantioselective deprotonation reactions. Synlett, (2), 177-180. https://doi.org/10.1055/s-0030-1259282