Rekowski, Szymon P. ; Wani, Aabid A. ; Conrad, Jürgen ; Bharatam, Prasad V. ; Frey, Wolfgang ; Beifuss, Uwe (2020) Transition metal-free diastereospecific synthesis of (Z)-2-arylidene-2,3-dihydrobenzo[b][1,4]dioxines by reaction of (Z)-1,2-dibromo-3-aryl-2-propenes with catechols Tetrahedron, 76 (42). p. 131482. ISSN 0040-4020
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Official URL: http://doi.org/10.1016/j.tet.2020.131482
Related URL: http://dx.doi.org/10.1016/j.tet.2020.131482
Abstract
A transition metal-free, diastereospecific reaction between substituted (Z)-1,2-dibromo-3-phenyl-2-propenes and substituted catechols using Cs2CO3 as a base at 140 °C for 18 h delivers exclusively substituted (Z)-2-arylidene-2,3-dihydrobenzo[b][1,4]dioxines in yields up to 89%. Experiments as well as quantum chemical calculations support the assumption that the one pot transformation proceeds as an intermolecular O-allylation/intramolecular O-vinylation.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier B.V. |
| Keywords: | O-Allylation; O-Vinylation; Benzodioxine; Diastereospecific Synthesis; DFT |
| ID Code: | 116252 |
| Deposited On: | 12 Apr 2021 08:35 |
| Last Modified: | 12 Apr 2021 08:35 |
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