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

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
Externally published	Yes

Fingerprint

Ethosuximide

Imides

Stereoselectivity

Carbonyl compounds

Iodides

Anions

Carbon

ethyl acetate

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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

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 journal › Article

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, vol. 44, no. 52, pp. 9303-9305. https://doi.org/10.1016/j.tetlet.2003.10.081

Abe T, Suzuki T, Sekiguchi K, Hosokawa S, Kobayashi S. Stereoselective construction of a quaternary carbon substituted with multifunctional groups: Application to the concise synthesis of (+)-ethosuximide. Tetrahedron Letters. 2003 Dec 22;44(52):9303-9305. https://doi.org/10.1016/j.tetlet.2003.10.081

Abe, Tomoaki ; Suzuki, Tatsuo ; Sekiguchi, Kazuhiko ; Hosokawa, Seijiro ; Kobayashi, Susumu. / Stereoselective construction of a quaternary carbon substituted with multifunctional groups : Application to the concise synthesis of (+)-ethosuximide. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 52. pp. 9303-9305.

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Access to Document

10.1016/j.tetlet.2003.10.081