Asymmetric synthesis of 3,4,5,6-tetrasubstituted piperidin-2-ones by three-component coupling

Stephen G. Davies*, Andrew D. Smith, Andrew R. Cowley

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

The asymmetric three-component coupling of α,β-unsaturated esters and alkylidene malonates initiated with a homochiral lithium amide proceeds with high levels of diastereoselectivity, with hydrogenation of the resultant α-substituted β-amino acid derivatives giving a range of differentially protected 3,4,5,6-tetrasubstituted piperidinones with four contiguous stereogenic centres.

Original languageEnglish
Pages (from-to)1957-1960
Number of pages4
JournalSynlett
Issue number11
DOIs
Publication statusPublished - 6 Sept 2004

Keywords

  • Conjugate addition
  • Oligomerisation
  • Piperidin-2-one
  • Three component coupling

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