Synthesis of optically active 6-amino-2-cycloheptenone as a convenient chiral building block for the preparation of 6-alkyl-2-cycloheptenone

被引：24

作者：

Koiwa, M ^{[1
]}

Hareau, GPJ ^{[1
]}

Morizono, D ^{[1
]}

Sato, F ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Kanagawa 2268501, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 22期

基金：

日本学术振兴会;

关键词：

asymmetric reactions; copper and compounds; enones; titanium and compounds;

D O I：

10.1016/S0040-4039(99)00711-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active 6-amino-2-cycloheptenone 5 has been prepared from ethyl 2(E),6-heptadienoate where the Michael addition of a chiral amine, Ti(II)-mediated intramolecular nucleophilic acyl substitution reaction and FeCl3-mediated ring expansion are the key steps. The compound 5 undergoes highly diastereoselective conjugate addition of a Grignard reagent in the presence of a catalytic amount of Li2Cu(CN)Cl-2 to provide the corresponding cis-adducts which, in turn, are converted into 6-alkyl substituted 2-cycloheptenones by treatment with p-TSA. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4199 / 4202

页数：4

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