Chiral enolate design

D. A. Evans, James M Takacs, L. R. McGee, M. D. Ennis, D. J. Mathre, J. Bartroli

Research output: Contribution to journalArticle

244 Citations (Scopus)

Abstract

The basic design features associated with the construc- tion of chiral propionate enolates will be presented. It has been found that amide and imide enolates derived from β-amino alcohols exhibit excellent levels of asymmetric induction in both alkylations and aldol condensations. For the aldol condensations metal structure was found to be of critical importance in the control of both erythro-threo -diastereoselection and chirality transfer. Both boron and zirconium enolates were found to be excellent substrates for the aldol process where > 98% enantioselection was observed.

Original languageEnglish (US)
Pages (from-to)1109-1127
Number of pages19
JournalPure and Applied Chemistry
Volume53
Issue number6
DOIs
StatePublished - Jan 1 1981
Externally publishedYes

Fingerprint

Condensation
Amino alcohols
Chirality
Alkylation
Amides
Zirconium
Amino Alcohols
Imides
Boron
Propionates
Substrates
Metals
3-hydroxybutanal

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Evans, D. A., Takacs, J. M., McGee, L. R., Ennis, M. D., Mathre, D. J., & Bartroli, J. (1981). Chiral enolate design. Pure and Applied Chemistry, 53(6), 1109-1127. https://doi.org/10.1351/pac198153061109

Chiral enolate design. / Evans, D. A.; Takacs, James M; McGee, L. R.; Ennis, M. D.; Mathre, D. J.; Bartroli, J.

In: Pure and Applied Chemistry, Vol. 53, No. 6, 01.01.1981, p. 1109-1127.

Research output: Contribution to journalArticle

Evans, DA, Takacs, JM, McGee, LR, Ennis, MD, Mathre, DJ & Bartroli, J 1981, 'Chiral enolate design', Pure and Applied Chemistry, vol. 53, no. 6, pp. 1109-1127. https://doi.org/10.1351/pac198153061109
Evans DA, Takacs JM, McGee LR, Ennis MD, Mathre DJ, Bartroli J. Chiral enolate design. Pure and Applied Chemistry. 1981 Jan 1;53(6):1109-1127. https://doi.org/10.1351/pac198153061109
Evans, D. A. ; Takacs, James M ; McGee, L. R. ; Ennis, M. D. ; Mathre, D. J. ; Bartroli, J. / Chiral enolate design. In: Pure and Applied Chemistry. 1981 ; Vol. 53, No. 6. pp. 1109-1127.
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