期刊
TETRAHEDRON
卷 75, 期 14, 页码 2246-2253出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.02.055
关键词
Bestmann-Ohira reagent; p-Quinone methides; 1,6-Conjugate addition; alpha-Diazo-beta-diarylphosphonates; cis-Stilbenyl phosphonates
资金
- SERB-DST India
- CSIR India
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 beta-disubstituted alpha-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. (C) 2019 Elsevier Ltd. All rights reserved.
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