17 research outputs found
3‑Imidoallenylphosphonates: <i>In Situ</i> Formation and β‑Alkoxylation
3-Imidoallenylphosphonates,
allenes bearing both an electron-withdrawing
and -donating group, were isolated for the first time. An alkoxy substituent
was introduced into these unprecedented intermediates in a one-pot
approach, yielding β-functionalized aminophosphonates in excellent
yields and short reaction times. The mechanistic insights gained are
important additions to the domain of allene chemistry. Addition of
biologically important molecules, including monoglycerides, amino
acids, and nucleosides, proves the general applicability of the developed
method
Preparation of tetrasubstituted 3-phosphonopyrroles through hydroamination: scope and limitations
Phosphonylated pyrroles were obtained by a ZnCl2-catalyzed 5-exo-dig hydroamination of propargylic enamines. These starting compounds were obtained in two steps from commercially available beta-ketophosphonates. The method tolerates a wide variety of substituents at the 1,2- and 5-position of the pyrrole, while further derivatization allows for the introduction of substituents at the 4-position via lithiation or halogenation