2-IMINOOXETANE CHEMISTRY .4. SYNTHESIS OF BETA-SUBSTITUTED PROPIONAMIDES

被引：9

作者：

BARBARO, G ^{[1
]}

BATTAGLIA, A ^{[1
]}

GIORGIANNI, P ^{[1
]}

机构：

[1] CNR,IST COMPOSTI CARBONIO CONTENENTI ETREOATOMI,I-40129 BOLOGNA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 04期

关键词：

D O I：

10.1021/jo00083a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-substituted propionamides (RCHXCR(1)R(2)CONHAr) were synthesized in high yields by addition of protic and aprotic Lewis acids (C6H5SO3H, CF3COOH, CH3COOH, HI, MgBr2, ZnI2, CH3OH, H2O,2,4,6-(NO2)(3)C6H2OH) to 2-iminooxetanes. Studies on the stereochemistry of the acid addition to unsymmetrically C3,C4-monosubstituted 2-iminooxetanes indicate that product distribution depends on the steric and electronic nature of the substitutents of the oxetane moiety as well as on the nucleophilicity of the conjugate base derived from the acid.

引用

页码：906 / 913

页数：8

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