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New potentially chelating chiral magnesium amide bases for use in enantioselective deprotonation reactions

Kerr, William and Middleditch, Michael and Watson, Allan (2011) New potentially chelating chiral magnesium amide bases for use in enantioselective deprotonation reactions. Synlett (2). pp. 177-180. ISSN 0936-5214

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Abstract

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.