Novel and stereoselective methods for the preparation of aromatic lactams via reductive coupling reactions mediated by SmI2

被引：38

作者：

Yoda, H ^{[1
]}

Matsuda, K ^{[1
]}

Nomura, H ^{[1
]}

Takabe, K ^{[1
]}

机构：

[1] Shizuoka Univ, Fac Engn, Dept Mol Sci, Hamamatsu, Shizuoka 4328561, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 11期

基金：

日本学术振兴会;

关键词：

cross-coupling reaction; samarium(II) diiodide; cyclic imide; stereoselective reduction; deoxygenation;

D O I：

10.1016/S0040-4039(00)00014-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Samarium(II) diiodide-mediated reductive cross-coupling of N-alkylated phthalimides with carbonyl compounds is shown to afford hydroxylated alpha-hydroxylactams, Ketoamides obtained by dehydration of these compounds through keto-enol tautomer isomerization were reduced with NaBH4 in a completely stereoselective manner in the presence of CeCl3 to give three-aromatic lactams as the sole product. Direct reductive deoxygenation of these alpha-hydroxylactam intermediates with Et3SiH in the presence of Lewis acid also displayed high stereoselectivity to afford the same threo-lactams exclusively. The mechanistic origins of this stereoselectivity are briefly documented. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1775 / 1779

页数：5

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