Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 12, Pages 5512-5515Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja300790x
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
- Grants-in-Aid for Scientific Research [23655035, 21106005, 21106001, 23350017] Funding Source: KAKEN
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Cationic iron(III) porphyrin was found to be an efficient catalyst for the highly chemoselective hetero-Diels Alder-type reaction of aldehydes with 1,3-dienes. The catalyzed process did not require the use of electron-deficient aldehydes such as glyoxylic acid derivatives or activated electron-rich 1,3-dienes such as Danishefslcy's diene and Rawal's diene. The high functional group tolerance and robustness of the catalyst were demonstrated. Further, the potential utility of the catalyst was demonstrated by performing the cycloaddition in the presence of water and by carrying out cycloaddition of an unactivated ketone such as cyclohexanone with a diene.
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