Catalytic asymmetric epoxidation of α,β-unsaturated carboxylic acid imidazolides and amides by lanthanide-BINOL complexes

Takashi Ohshima, Tetsuhiro Nemoto, Shin Ya Tosaki, Hiroyuki Kakei, Vijay Gnanadesikan, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

Abstract

Highly enantioselective catalytic asymmetric epoxidation of α,β-unsaturated carboxylic acid imidazolides and simple amides was developed. In the presence of 5-10mol% of lanthanide-BINOL complexes, the reaction proceeded smoothly with high substrate generality. In particular, in the cases of α,β-unsaturated amides, there was nearly perfect enantioselectivity (>99% ee). The corresponding epoxides were successfully transformed into many types of useful chiral compounds such as α,β-epoxy esters, α,β-epoxy amides, α,β-epoxy aldehydes, α,β-epoxy β-keto ester, and α- and β-hydroxy carbonyl compounds. B3LYP density functional studies were performed to predict substrate reactivity.

Original languageEnglish
Pages (from-to)10485-10497
Number of pages13
JournalTetrahedron
Volume59
Issue number52
DOIs
Publication statusPublished - Dec 22 2003
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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