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Al-Rashid ZF Johnson WL Hsung RP Wei Y Yao PY Liu R Zhao K 《The Journal of organic chemistry》2008,73(22):8780-8784
A de novo preparation of alpha-keto-imides via ynamide oxidation is described. With a number of alkyne oxidation conditions screened, a highly efficient RuO2-NaIO4 mediated oxidation and a DMDO oxidation have been identified to tolerate a wide range of ynamide types. In addition to accessing a wide variety of alpha-keto-imides, the RuO2-NaIO4 protocol provides a novel entry to the vicinal tricarbonyl motif via oxidation of push-pull ynamides, and imido acylsilanes from silyl-substituted ynamides. Chemoselective oxidation of ynamides containing olefins can be achieved by using DMDO, while the RuO2-NaIO4 protocol is not effective. These studies provide further support for the synthetic utility of ynamides. 相似文献
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Ko C Hsung RP Al-Rashid ZF Feltenberger JB Lu T Yang JH Wei Y Zificsak CA 《Organic letters》2007,9(22):4459-4462
A stereoselective halo-etherification of chiral enamides is described here. This work provides an approach to halogen containing cyclic ethers and reveals further mechanistic insights to the chemistry of chiral enamides. 相似文献
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The reaction profile of DMDO oxidations of ynamides is described. This work illustrates the first examples of highly diastereoselective intramolecular cyclopropanations of a push-pull carbene derived from alkyne oxidation. In addition, the ynamide oxidation provides facile access to ketoimides and reveals mechanistic insights into the chemistry of electronically biased oxirenes. 相似文献
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