Enantio- and regiocontrol in palladium- and tungsten-catalyzed allylic substitutions

R Pretot*, GC Lloyd-Jones, A Pfaltz

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Tungsten catalysts with chiral phosphinooxazoline ligands react with 3-aryl-2-propenyl diethyl phosphates and the sodium salt of dimethyl malonate to give the corresponding chiral substitution products with regioselectivities of 3-24:1 and 88-96% ee. A new class of chiral P,N-ligands has been developed which allow efficient regio- and enantiocontrol in analogous Pd-catalyzed allylic substitutions of 1- and 3-aryl-2-propenyl acetates with dimethyl malonate.

Original languageEnglish
Pages (from-to)1035-1040
Number of pages6
JournalPure and applied chemistry
Volume70
Issue number5
Publication statusPublished - May 1998
Event9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-9) - GOTTINGEN, Germany
Duration: 20 Jul 199725 Jul 1997

Keywords

  • ASYMMETRIC CATALYSIS
  • NUCLEOPHILIC-ATTACK
  • CHIRAL LIGANDS
  • ALKYLATIONS
  • AMINATION
  • ALCOHOLS

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