One-pot synthesis of five-membered cyclic thioethers or ethers via intramolecular nitrile oxide-olefin cycloaddition (INOC) or intramolecular alkoxycarbonyl nitronate-olefin cycloaddition (IAOC) by the use of methyl chloroformate

Ming Chung Yan, Jing Yuan Liu, Wen Wei Lin, Kuo Hsi Kao, Ju Tsung Liu, Jeong Jiunn Jang, Ching Fa Yao*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

18 引文 斯高帕斯(Scopus)

摘要

Reaction of β-nitrostyrenes 1 with allyl mercaptan 2 in the presence of triethylamine generated unsaturated nitro sulfides 3 and then the solution was treated with methyl chloroformate (MCF) and was refluxed to obtain [3.3.0]bicyclic products trans-6 and cis-6 in one-pot. The ratios of trans- 6:cis-6 were from 1.1:1 to 1.8:1 and the mechanism of the formation 6 is proposed to proceed through the formation of nitrile oxides 5 to undergo intramolecular nitrile oxide-olefin cycloaddition (INOC). Nitronates 16, prepared from 1 with allyl alcohol and base, can be converted into methoxycarbonyl nitronates 22 by treating the solution with methyl chloroformate and catalytic amount of 4-dimethylaminopyridine (DMAP) in the presence of different amounts of triethylamine. Intermediates 22 can either undergo intramolecular alkoxycarbonyl nitronate-olefin cycloaddition (IAOC) to generate highly stereoselective product trans-14 or undergo INOC to yield trans-14 and cis-14. The application of this improved methodology to synthesize different heterocyclic products 10, 26, and 27 is reported.

原文英語
頁(從 - 到)12493-12514
頁數22
期刊Tetrahedron
55
發行號43
DOIs
出版狀態已發佈 - 1999 十月 22

ASJC Scopus subject areas

  • 生物化學
  • 藥物發現
  • 有機化學

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