Journal
TETRAHEDRON LETTERS
Volume 54, Issue 5, Pages 377-380Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.10.129
Keywords
Olefin metathesis; Amine; Enamine; Oxidation; Alkaloid
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Funding
- Cabinet Office, Government of Japan through its Funding Program for Next Generation World-Leading Researchers [LS008]
- Tohoku University G-COE program 'IREMC'
- [24790003]
- Grants-in-Aid for Scientific Research [24790003] Funding Source: KAKEN
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During synthetic studies toward strictamine, unexpected oxidation of tertiary amine to enamine was observed in ring-closing olefin metathesis (RCM) using Hoveyda-Grubbs 2nd catalyst. Control experiments under deoxygenated conditions indicated Ru-catalyst and electron deficient 1,4-benzoquinone additive promoted oxidation. The desired RCM reaction took place selectively under microwave irradiation by suppression of oxidation of amine. (C) 2012 Elsevier Ltd. All rights reserved.
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