Magnesium amide base-mediated enantioselective deprotonation processes

W.J. Kerr, K.W. Henderson, J.H. Moir

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

A novel homochiral magnesium bisamide has been readily prepared and, following careful optimisation, this species has been shown to react efficiently with a series of prochiral 4-substituted cyclohexanones in the presence of TMSCl to give the corresponding silyl enol ethers in enantiomeric ratios of up to 95:5. Additionally, the same chiral base system has been shown to be highly effective in the desymmetrisation of cis-2,6-disubstituted cyclohexanones, providing excellent levels of both conversion and enantioselection (up to >99.5:0.5 er). Furthermore, the magnesium bisamide has also been shown to mediate a kinetic resolution process with the corresponding trans-disubstituted substrates, allowing access to enantioenriched enol ethers and ketones.
LanguageEnglish
Pages4573-4587
Number of pages15
JournalTetrahedron
Volume58
Issue number23
DOIs
Publication statusPublished - 2002

Fingerprint

Cyclohexanones
Deprotonation
Ethers
Amides
Magnesium
Ketones
Kinetics
Substrates

Keywords

  • deprotonation processes
  • enantioselective deprotonation processes
  • magnesium amides

Cite this

Kerr, W.J. ; Henderson, K.W. ; Moir, J.H. / Magnesium amide base-mediated enantioselective deprotonation processes. In: Tetrahedron. 2002 ; Vol. 58, No. 23. pp. 4573-4587.
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Magnesium amide base-mediated enantioselective deprotonation processes. / Kerr, W.J.; Henderson, K.W.; Moir, J.H.

In: Tetrahedron, Vol. 58, No. 23, 2002, p. 4573-4587.

Research output: Contribution to journalArticle

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KW - deprotonation processes

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