Stereoselective construction of a quaternary carbon substituted with multifunctional groups: Application to the concise synthesis of (+)-ethosuximide

Tomoaki Abe, Tatsuo Suzuki, Kazuhiko Sekiguchi, Seijiro Hosokawa, Susumu Kobayashi

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

Synthetically useful β,γ-unsaturated carbonyl compounds having a quaternary carbon at the α-position were prepared with high stereoselectivity by the reaction of a dienolate anion derived from α,β-unsaturated imide having a chiral auxiliary and electrophiles (ethyl acetate and allyl iodide as the C2 and C3 unit, respectively). This method was applied to a short asymmetric synthesis of (+)-ethosuximide.

Original languageEnglish
Pages (from-to)9303-9305
Number of pages3
JournalTetrahedron Letters
Volume44
Issue number52
DOIs
Publication statusPublished - 2003 Dec 22
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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