Racemic and asymmetric cobalt-catalysed reductive aldol couplings of alpha,beta-unsaturated amides with ketones

Ralph J. R. Lumby, Pekka M. Joensuu, Hon Wai Lam

Research output: Contribution to journalArticlepeer-review

Abstract

In the presence of diethylzinc as a stoichiometric reductant, substoichiometric quantities of an appropriate cobalt source catalyse diastereoselective reductive aldol coupling reactions of alpha,beta-unsaturated amides with ketones. The use of a readily available oxazolidine as a chiral auxiliary imparts high levels of asymmetric induction in these reactions. (C) 2008 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)7729-7740
Number of pages12
JournalTetrahedron
Volume64
Issue number33
DOIs
Publication statusPublished - 11 Aug 2008

Keywords / Materials (for Non-textual outputs)

  • KETENE SILYL ACETAL
  • CHIRAL LEWIS-ACIDS
  • ENANTIOSELECTIVE SYNTHESIS
  • PYRUVATE ESTERS
  • STEREOSELECTIVE-SYNTHESIS
  • STOICHIOMETRIC REDUCTANT
  • COPPER(II) COMPLEXES
  • CONJUGATE ADDITION
  • CARBONYL-COMPOUNDS
  • ENOL ETHER

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