Beilstein J. Org. Chem.2016,12, 2906–2915, doi:10.3762/bjoc.12.290
reaction; γ-ketoallylphosphonate; organophosphorus chemistry; Introduction
Phosphonates and their derivatives are an important class of substances that have a wide range of applications in numerous areas such as medicinal [1][2][3] and agricultural chemistry [4][5]. Among them, multifunctional derivatives
second β’-conjugate addition of triethyl phosphite onto I (iii), followed by the release of DMAP would provide the phosphonium intermediate II (iv). Finally, the hydroxide ion is expected to react with II via an Arbuzov rearrangement to provide the desired γ-ketoallylphosphonate 2a (v) (Scheme 3).
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Graphical Abstract
Scheme 1:
Synthesis of allylphosphonates from acyclic MBH adducts.