AI Article Synopsis
- * A specific reaction described is the Luche reduction of a primary phosphonate, leading to the formation of γ-hydroxyallylphosphonates, which subsequently react with tosylamines to produce S2-type products with yields of 63 to 70%.
- * The method also allows for the conversion of the resulting alcohol to an acetate, which can be transformed into γ-aminoallylphosphonates using cerium (Ce
Article Abstract
An efficient synthesis of a series of γ-ketoallylphosphonates through a direct conversion of both primary and secondary Morita-Baylis-Hillman (MBH) alcohols by trialkyl phosphites with or without DMAP, used as additive, and under solvent-free conditions, is described herein for the first time. Subsequently, a highly regioselective Luche reduction of the primary phosphonate (R = H) gave the corresponding γ-hydroxyallylphosphonate that further reacted with tosylamines in the presence of diiodine (15 mol %) as a catalyst, affording the corresponding S2-type products in 63 to 70% isolated yields. Alternatively, the alcohol produced the corresponding acetate which, mediated by Ce(III), was successfully converted into the corresponding γ-aminoallylphosphonates .
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238584 | PMC |
| http://dx.doi.org/10.3762/bjoc.12.290 | DOI Listing |
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