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 |
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ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
Cite this
Research on unique masked ortho-benzoquinone, monohemiaminal : Synthesis and reactions. / Matsumoto, Yuri; Nakamura, Akihiko; Saito, Emi; Nakada, Masahisa.
In: Heterocycles, Vol. 97, No. 1, 01.01.2018, p. 232-252.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Research on unique masked ortho-benzoquinone, monohemiaminal
T2 - Synthesis and reactions
AU - Matsumoto, Yuri
AU - Nakamura, Akihiko
AU - Saito, Emi
AU - Nakada, Masahisa
PY - 2018/1/1
Y1 - 2018/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85064562435&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85064562435&partnerID=8YFLogxK
U2 - 10.3987/COM-17-S(T)11
DO - 10.3987/COM-17-S(T)11
M3 - Article
AN - SCOPUS:85064562435
VL - 97
SP - 232
EP - 252
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 1
ER -