STEREOSELECTIVE PROTONATION OF CARBANIONS .3. 1,3-DIOXOLAN-4-ONES AND 1,3-OXAZOLIDINE-4-ONES - SYNTHESES AND DIASTEREOSELECTIVE PROTONATION OF THEIR ANIONS

被引：7

作者：

HUNIG, S ^{[1
]}

KEITA, Y ^{[1
]}

PETERS, K ^{[1
]}

VONSCHNERING, HG ^{[1
]}

机构：

[1] MAX PLANCK INST FESTKORPERFORSCHUNG,D-70506 STUTTGART,GERMANY

来源：

CHEMISCHE BERICHTE | 1994年 / 127卷 / 08期

关键词：

1,3-DIOXALAN-4-ONES; 1,3-OXAZOLIDINE 4-ONES; DIASTEREOSELECTIVITY; PROTONATION; ENOLATES;

D O I：

10.1002/cber.19941270824

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dioxolonanones 3 and oxazolidinones 4 are synthesized by different methods together with the silyl enol ether 3a(Si). The configuration of their diastereomers is determined by H-1-NMR spectroscopy and relative retention times (vpc), backed by a crystal structure analysis of cis-3d. Protonation of 3aLi and 4aLi by different OH and CH proton sources in THF at -78-degrees-C occurs by kinetic product control yielding always ca. 70-90% of the cis isomers. Exchange of the cation in 3Li by potassium or addition of several Lewis acids does not effect the cis/trans relations. Obviously, even the steric effect Of d methyl group in 2-position of 3Li and 4Li dominates so strongly that the effect of other parameters are suppressed.

引用

页码：1495 / 1500

页数：6

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