Vinyl Benzenes as Dienes in Mild Solid-Phase Diels-Alder Reactions
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- 作者：Sengen Sun ; Ignatius J. Turchi ; Dawei Xu ; and William V. Murray
- 刊名：Journal of Organic Chemistry
- 出版年：2000
- 出版时间：April 21, 2000
- 年：2000
- 卷：65
- 期：8
- 页码：2555 - 2559
- 全文大小：99K
- 年卷期：v.65,no.8(April 21, 2000)
- ISSN：1520-6904
文摘
Wang resin-bound intermediates derived from Fmoc-L-phenylalaninal and Fmoc-L-valinal, and aresin supported Horner-Wadsworth-Emmons reaction, were treated with cinnamaldehydederivatives, acetic acid, and borohydride to give secondary amines which were subsequentlybenzoylated to afford various derivatives of 3. Heating 3 at 95 
C induced cycloaddition reactionsand produced 4 as the major product. Compounds 3 which were derived from 4-methoxycinnamaldehyde were more reactive, but did not give 4 and 4-7g. The direct cleavage of 3b using TFA ledto the isolation of cycloaddition-demethylation product 10. The derivative of 3, which containedan electron-withdrawing nitro group on the phenyl ring, produced a single diastereomer of 4. TheDiels-Alder cycloaddition between two electron-deficient counterparts showed similar reactivityto that of the reactions which have a normal complementary electron-demand.
C induced cycloaddition reactionsand produced 4 as the major product. Compounds 3 which were derived from 4-methoxycinnamaldehyde were more reactive, but did not give 4 and 4-7g. The direct cleavage of 3b using TFA ledto the isolation of cycloaddition-demethylation product 10. The derivative of 3, which containedan electron-withdrawing nitro group on the phenyl ring, produced a single diastereomer of 4. TheDiels-Alder cycloaddition between two electron-deficient counterparts showed similar reactivityto that of the reactions which have a normal complementary electron-demand.