Application of (S)- and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions

Chaozhong Cai, Takeshi Yamada, Rohit Tiwari, Victor J. Hruby, Vadim A. Soloshonok

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

Methyl N-(E-enoyl)pyroglutamates, derived from inexpensive and readily available in both enantiomeric forms pyroglutamic acid were found to be an efficient Michael acceptors in the addition reactions with nucleophilic glycine equivalent allowing for an efficient practical asymmetric synthesis of β-substituted pyroglutamic acids and related compounds.

Original languageEnglish (US)
Pages (from-to)6855-6858
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number37
DOIs
StatePublished - Sep 6 2004

Keywords

  • Asymmetric synthesis
  • Michael addition
  • Ni(II)-complex
  • Pyroglutamate

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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