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

被引:32
作者
Abe, T
Suzuki, T
Sekiguchi, K
Hosokawa, S
Kobayashi, S [1 ]
机构
[1] Tokyo Univ Sci, Fac Pharmaceut Sci, Noda, Chiba 2788510, Japan
[2] Tokyo Univ Sci, Frontier Res Ctr Genom Drug Discovery, Noda, Chiba 2788510, Japan
关键词
D O I
10.1016/j.tetlet.2003.10.081
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthetically useful beta,gamma-unsaturated carbonyl compounds having a quaternary carbon at the alpha-position were prepared with high stereoselectivity by the reaction of a dienolate anion derived from alpha,beta-unsaturated imide having a chiral auxiliary and electrophiles (ethyl acetate and allyl iodide as the C-2 and C-3 unit, respectively). This method was applied to a short asymmetric synthesis of (+)-ethosuximide. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9303 / 9305
页数:3
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