Details
| Original language | English |
|---|---|
| Pages (from-to) | 6951-6956 |
| Number of pages | 6 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2017 |
| Issue number | 46 |
| Publication status | Published - 15 Dec 2017 |
Abstract
Benzil and its derivatives naphthil and pyridil have been found to undergo a dianionic oxy-Cope rearrangement upon reaction with 2-lithio-4,5-dihydrofuran to give 3,3′-octahydrobifuranyls selectively as the meso diastereomers. The diastereoselectivity is explained based on the reaction mechanism and the conformation of the starting material. 4,4′-Di-tertbutylbenzil gave the respective intramolecular aldol adduct, whose relative configuration was determined by NOE experiments.
Keywords
- Benzil, Diketones, Heterocycles, Oxygen heterocycles, Rearrangement
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, Vol. 2017, No. 46, 15.12.2017, p. 6951-6956.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Dianionic oxy-cope rearrangement with benzil derivatives
T2 - Meso-selective 3,3-coupling of two tetrahydrofuran moieties
AU - Abdelhamid, Ismail Abdelshafy
AU - Abdelmoniem, Amr Mohamed
AU - Fohrer, Jörg
AU - Bardenhorst, Iris
AU - Wartchow, Rudolf
AU - Butenschön, Holger
N1 - Funding Information: I. A. A. and A. M. A. thank the Alexander von Humboldt Foundation for postdoctoral fellowship and for short-term-visit grants. We thank Dr. Gerald Dräger, Institut für Organische Chemie, Leibniz Universität Hannover, for help with the crystal-structure analysis of meso-15. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.
PY - 2017/12/15
Y1 - 2017/12/15
N2 - Benzil and its derivatives naphthil and pyridil have been found to undergo a dianionic oxy-Cope rearrangement upon reaction with 2-lithio-4,5-dihydrofuran to give 3,3′-octahydrobifuranyls selectively as the meso diastereomers. The diastereoselectivity is explained based on the reaction mechanism and the conformation of the starting material. 4,4′-Di-tertbutylbenzil gave the respective intramolecular aldol adduct, whose relative configuration was determined by NOE experiments.
AB - Benzil and its derivatives naphthil and pyridil have been found to undergo a dianionic oxy-Cope rearrangement upon reaction with 2-lithio-4,5-dihydrofuran to give 3,3′-octahydrobifuranyls selectively as the meso diastereomers. The diastereoselectivity is explained based on the reaction mechanism and the conformation of the starting material. 4,4′-Di-tertbutylbenzil gave the respective intramolecular aldol adduct, whose relative configuration was determined by NOE experiments.
KW - Benzil
KW - Diketones
KW - Heterocycles
KW - Oxygen heterocycles
KW - Rearrangement
UR - http://www.scopus.com/inward/record.url?scp=85038222438&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201701397
DO - 10.1002/ejoc.201701397
M3 - Article
AN - SCOPUS:85038222438
VL - 2017
SP - 6951
EP - 6956
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 46
ER -