DIMETHYLDIOXIRANE OXIDATION OF ENAMINES - 1ST SPECTRAL EVIDENCE FOR ENAMINE OXIDES BY STABILIZATION THROUGH N-SILYLATION

被引：27

作者：

ADAM, W

AHRWEILER, M

PAULINI, K

REISSIG, HU

VOERCKEL, V

机构：

[1] TH MERSEBURG,INST TECH CHEM,O-4200 MERSEBURG,GERMANY

[2] UNIV WURZBURG,INST ORGAN CHEM,W-8700 WURZBURG,GERMANY

[3] TH DARMSTADT,INST ANORGAN CHEM,W-6100 DARMSTADT,GERMANY

来源：

CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 12期

关键词：

EPOXIDATION; ENAMINES; N-SILYLATED; INDOLES; EPOXIDES; DISILYLAMINOXIDES; KETONES ALPHA-AMINO; INDOLINONES; DIMETHYLDIOXIRANE;

D O I：

10.1002/cber.19921251217

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The oxygen transfer to the enamines 1a - f by dimethyldioxirane (DMD) in acetone solution leads to the alpha-amino epoxides 2a - f. The stability of the alpha-amino epoxides 2a - f depends only on the type of substitution at the nitrogen atom. Thus, while the epoxides 2a, b could be characterized spetroscopically, the epoxidation of the enamines 1c - f resulted in the corresponding alpha-amino ketone 3c (hydride shift) and the amides 4d - f (alkyl shift). The alpha-[bis(trimethylsilyl)]amino epoxides 2a, b represent the first observable enamine oxides and emphasize the value of stabilizing such labile epoxides through disilylation of the enamine nitrogen atom.

引用

页码：2719 / 2721

页数：3