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

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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 (https://doi.org/10.1055/s-0030-1259282)

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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.

ORCID iDs

Kerr, William ORCID logoORCID: https://orcid.org/0000-0002-1332-785X, Middleditch, Michael and Watson, Allan;
CORE (COnnecting REpositories)