Abstract
Synthesis of ortho-benzoquinone monohemiaminals via the oxidative dearomatization/O-cyclization cascades of phenols bearing an ortho substituent derived from an amino alcohol with PIDA is described. The cascade reactions of substrates bearing a chiral substituent were found to proceed in a stereoselective manner. The Diels-Alder reactions of the ortho-benzoquinone monohemiaminals proceed in a highly stereoselective manner. The oxidative dearomatization/O-cyclization cascade affording the ortho-benzoquinone monohemiaminal had never been reported; hence, there is still ample scope for further investigation.
| Original language | English |
|---|---|
| Pages (from-to) | 232-252 |
| Number of pages | 21 |
| Journal | Heterocycles |
| Volume | 97 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2018 Jan 1 |
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
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Matsumoto, Y., Nakamura, A., Saito, E., & Nakada, M. (2018). Research on unique masked ortho-benzoquinone, monohemiaminal: Synthesis and reactions. Heterocycles, 97(1), 232-252. https://doi.org/10.3987/COM-17-S(T)11