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

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.

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• Item metadata

  Item type:	Article
  ID code:	28916
  Dates:	Date Event 2011 Published
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	30 Mar 2011 08:51
  Last modified:	08 Apr 2024 18:45
  Related URLs:	Scopus publication
  URI:	https://strathprints.strath.ac.uk/id/eprint/28916