Chiral enolate design

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

Research output: Contribution to journalArticle

247 Scopus citations

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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    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