Synthesis of β-and β,β-substituted Morita-Baylis-Hillman adducts using a two-step protocol

David I. MaGee, Same Ratshonka, Jessica McConaghy, Maggie Hood

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The synthesis of a large number of β-and β,β-substituted keto esters was successful by the use of the Knoevenagel condensation reaction. The stereoselectivity of these reactions was improved by alteration of various substituent groups. Although there were few examples of complete Z selectivity, the use of tert-butyl acetoacetate with either aromatic or aliphatic aldehydes afforded Z selectivity. The selective reductions of these substituted keto esters was successfully achieved by using a combination of NaBH 4 and CeCl 3·7H 2O or Yb(OTf) 3, which allowed a facile synthesis of a large number of stereochemically pure substituted Morita-Baylis-Hillman adducts, including β,β-substituted adducts.

Original languageEnglish
Pages (from-to)450-463
Number of pages14
JournalCanadian Journal of Chemistry
Volume90
Issue number5
DOIs
Publication statusPublished - May 1 2012

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Esters
Stereoselectivity
Condensation reactions
Aldehydes
acetoacetic acid
ytterbium(III) triflate

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

MaGee, David I. ; Ratshonka, Same ; McConaghy, Jessica ; Hood, Maggie. / Synthesis of β-and β,β-substituted Morita-Baylis-Hillman adducts using a two-step protocol. In: Canadian Journal of Chemistry. 2012 ; Vol. 90, No. 5. pp. 450-463.
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Synthesis of β-and β,β-substituted Morita-Baylis-Hillman adducts using a two-step protocol. / MaGee, David I.; Ratshonka, Same; McConaghy, Jessica; Hood, Maggie.

In: Canadian Journal of Chemistry, Vol. 90, No. 5, 01.05.2012, p. 450-463.

Research output: Contribution to journalArticle

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