期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 9, 页码 3278-3285出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo900135t
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资金
- Scientific Research (KAKENHI).
- Takeda Science Foundation
- Grants-in-Aid for Scientific Research [21390031] Funding Source: KAKEN
We previously achieved NHC-mediated preparation of ester-type fluoroalkene dipeptide isosteres (ES-FADIs, 4) by an intramolecular redox reaction. In the present study, a cyanide ion-mediated reaction was successfully applied to the conversions of gamma,gamma-difluoro-alpha,beta-enoylsilane 1 or 2 to amide-type fluoroalkene isosteres (AM-FADIs, 5 or 6). The use of catalytic cyanide ion allowed synthesis of chiral auxiliary incorporated FADI 15b which was then subjected to a diastereoselective alpha-alkylation reaction to yield alpha-substituted FADIs 17. Furthermore, the presented amidation protocol was used for straightforward incorporation of FADI into peptidyl resin.
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