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 › peer-review

35 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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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 › peer-review

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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.",

author = "Tomoaki Abe and Tatsuo Suzuki and Kazuhiko Sekiguchi and Seijiro Hosokawa and Susumu Kobayashi",

note = "Funding Information: This work was supported in part by the Fujisawa Foundation (S.H.) and Grant-in-Aids for Scientific Research from the Ministry of Education, Culture, Sports, and, Science and Technology, Japan. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.",

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AU - Hosokawa, Seijiro

AU - Kobayashi, Susumu

N1 - Funding Information: This work was supported in part by the Fujisawa Foundation (S.H.) and Grant-in-Aids for Scientific Research from the Ministry of Education, Culture, Sports, and, Science and Technology, Japan. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.

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N2 - 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.

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

Abstract

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