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

William Kerr, Michael Middleditch, Allan Watson

Research output: Contribution to journalArticle

8 Citations (Scopus)

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.
LanguageEnglish
Pages177-180
Number of pages3
JournalSynlett
Issue number2
DOIs
Publication statusPublished - 2011

Fingerprint

Deprotonation
Chelation
Amides
Magnesium
Thiophenes
Amines
Substrates
cyclohexanone

Keywords

  • asymmetric synthesis
  • enantioselectivity
  • heterocycles
  • enolate
  • magnesium

Cite this

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New potentially chelating chiral magnesium amide bases for use in enantioselective deprotonation reactions. / Kerr, William; Middleditch, Michael; Watson, Allan.

In: Synlett, No. 2, 2011, p. 177-180.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Middleditch, Michael

AU - Watson, Allan

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N2 - 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.

AB - 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.

KW - asymmetric synthesis

KW - enantioselectivity

KW - heterocycles

KW - enolate

KW - magnesium

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