Pati, Soumyaranjan ; Namboothiri, Irishi N.N. (2019) Deacylative 1,6-addition of Bestmann-Ohira reagent to p-quinone methides for the synthesis of α-diazo-β-diarylphosphonates and cis-stilbenyl phosphonates Tetrahedron, 75 (14). pp. 2246-2253. ISSN 0040-4020
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Official URL: http://doi.org/10.1016/j.tet.2019.02.055
Related URL: http://dx.doi.org/10.1016/j.tet.2019.02.055
Abstract
The role of Bestmann-Ohira Reagent (BOR) as a conjugate addition partner is reported for the first time. Deacylation of BOR in the presence of ethanolic KOH and 1,6-addition of the resulting diazophosphonate anion to p-quinone methides (PQMs) provides β-disubstituted α-diazophosphonates in good to excellent yields in most cases. Such 1,6-adducts further undergo Rh-catalyzed elimination of the diazo group and 1,2-migration of the phenolic group to afford cis-stilbenylphosphonates with high E-selectivity. The migration of the phenolic group presumably takes place via a spirocyclopropane intermediate derived from the Rh-carbenoid.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Bestmann-Ohira Reagent; p-quinone Methides 1,6-Conjugate Addition; α-diazo-β-diarylphosphonates; cis-Stilbenyl Phosphonates. |
| ID Code: | 121308 |
| Deposited On: | 14 Jul 2021 08:46 |
| Last Modified: | 14 Jul 2021 08:46 |
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