Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 12623–12629 |
| Seitenumfang | 7 |
| Fachzeitschrift | Journal of Organic Chemistry |
| Jahrgang | 88 |
| Ausgabenummer | 17 |
| Frühes Online-Datum | 18 Aug. 2023 |
| Publikationsstatus | Veröffentlicht - 1 Sept. 2023 |
Abstract
The development of new methods and protocols for the synthesis of biologically active substances remains one of the most important pillars in organic chemistry, and one of these privileged structural motifs are allylic alcohols. The method of choice to date for the synthesis of these is the Nozaki-Hiyama-Takai-Kishi reaction. We describe here a valuable alternative to the synthesis of allylic alcohols via 1,2-metallate rearrangement. In this work, various vinyl boronic esters with different functional groups have been applied in the Hoppe-Matteson-Aggarwal reaction. In addition, two monoterpenoids were constructed via this convergent synthetic strategy.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Organische Chemie
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in: Journal of Organic Chemistry, Jahrgang 88, Nr. 17, 01.09.2023, S. 12623–12629.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - 1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols
AU - Linne, Yannick
AU - Lohrberg, Daniel
AU - Struwe, Henry
AU - Linne, Elvira
AU - Stohwasser, Anastasia
AU - Kalesse, Markus
N1 - Funding Information: This work was supported by the Deutsche Forschungsgemeinschaft (DFG) KA 913/24–1.
PY - 2023/9/1
Y1 - 2023/9/1
N2 - The development of new methods and protocols for the synthesis of biologically active substances remains one of the most important pillars in organic chemistry, and one of these privileged structural motifs are allylic alcohols. The method of choice to date for the synthesis of these is the Nozaki-Hiyama-Takai-Kishi reaction. We describe here a valuable alternative to the synthesis of allylic alcohols via 1,2-metallate rearrangement. In this work, various vinyl boronic esters with different functional groups have been applied in the Hoppe-Matteson-Aggarwal reaction. In addition, two monoterpenoids were constructed via this convergent synthetic strategy.
AB - The development of new methods and protocols for the synthesis of biologically active substances remains one of the most important pillars in organic chemistry, and one of these privileged structural motifs are allylic alcohols. The method of choice to date for the synthesis of these is the Nozaki-Hiyama-Takai-Kishi reaction. We describe here a valuable alternative to the synthesis of allylic alcohols via 1,2-metallate rearrangement. In this work, various vinyl boronic esters with different functional groups have been applied in the Hoppe-Matteson-Aggarwal reaction. In addition, two monoterpenoids were constructed via this convergent synthetic strategy.
UR - http://www.scopus.com/inward/record.url?scp=85169165928&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.3c01309
DO - 10.1021/acs.joc.3c01309
M3 - Article
AN - SCOPUS:85169165928
VL - 88
SP - 12623
EP - 12629
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 17
ER -