Stereoselective construction of a quaternary carbon substituted with multifunctional groups: application to the concise synthesis of (+)-ethosuximide
Stereoselective construction of a quaternary carbon substituted with multifunctional groups: application to the concise synthesis of (+)-ethosuximide
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DOI：
10.1016/j.tetlet.2003.10.081
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发表时间：
2003-12-22
影响因子：
1.8
通讯作者：
Kobayashi, S
中科院分区：
文献类型：
--
作者：
Abe, T;Suzuki, T;Kobayashi, S
由具有手性助剂的α，β-不饱和亚胺衍生的二烯酸酯阴离子与亲电试剂(乙酸乙酯和烯丙基碘化物分别作为C-2和C-3单元)反应，以高的立体选择性合成了合成上有用的具有α-位的季碳的β，伽马-不饱和羰基化合物。将该方法应用于(+)-乙硫胺的短不对称合成。(C)2003爱思唯尔有限公司。保留所有权利。
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.