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

doi:10.1016/j.tetlet.2003.10.081

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

School of Advanced Science and Engineering

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	9303-9305
Number of pages	3
Journal	Tetrahedron Letters
Volume	44
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2003.10.081
Publication status	Published - 2003 Dec 22

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ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Abe, T., Suzuki, T., Sekiguchi, K., Hosokawa, S., & Kobayashi, S. (2003). Stereoselective construction of a quaternary carbon substituted with multifunctional groups: Application to the concise synthesis of (+)-ethosuximide. Tetrahedron Letters, 44(52), 9303-9305. https://doi.org/10.1016/j.tetlet.2003.10.081

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Access to Document

10.1016/j.tetlet.2003.10.081