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 journalArticle

33 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

Fingerprint

Ethosuximide
Imides
Stereoselectivity
Carbonyl compounds
Iodides
Anions
Carbon
ethyl acetate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereoselective construction of a quaternary carbon substituted with multifunctional groups : Application to the concise synthesis of (+)-ethosuximide. / Abe, Tomoaki; Suzuki, Tatsuo; Sekiguchi, Kazuhiko; Hosokawa, Seijiro; Kobayashi, Susumu.

In: Tetrahedron Letters, Vol. 44, No. 52, 22.12.2003, p. 9303-9305.

Research output: Contribution to journalArticle

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