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 |
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry