ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO CHALCONES CATALYZED BY CHIRAL NI(II) AMINOALCOHOL COMPLEXES

AHM DEVRIES, JFGA JANSEN, BL FERINGA

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Conjugate addition of diethylzinc to chalcones is catalysed by complexes prepared in situ from Ni(acac)(2) and cis-exo-N,N-dialkyl-3-aminoisoborneols or (+)-cis-endo-N,N-dimethyl-3-aminoborneol ((+)- DAB) (13b). The products are obtained with enantioselectivities up to 84 %. When scalemic (-)-cis-exo-N,N-dimethyl-3-aminoisoborneol ((-)-DAIB) (3c) was employed in the reaction a positive nonlinear relationship was found. Several factors which govern catalyst activity and enantioselectivity have been investigated.

Original languageEnglish
Pages (from-to)4479-4491
Number of pages13
JournalTetrahedron
Volume50
Issue number15
Publication statusPublished - 11-Apr-1994

Keywords

  • GRIGNARD-REAGENTS
  • ASYMMETRIC INDUCTION
  • ORGANOZINC REAGENTS
  • ENONES
  • ALDEHYDES
  • DIALKYLZINCS
  • KETONES
  • LIGAND
  • AMPLIFICATION

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