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Title: Efficient Oxidative Resolution of 1-Phenylphosphol-2-Ene and Diels–Alder Synthesis of Enantiopure Bicyclic and Tricyclic P-Stereogenic C-P Heterocycles
Authors: Demchuk, Oleg M.
Pietrusiewicz, Kazimierz Michał
Koprowski, Marek
Drzazga, Zbigniew
Parcheta, Renata
Łastawiecka, Elżbieta
Justyniak, Iwona
Keywords: P-stereogenicity; 1-phenylphosphol-2-ene 1-oxide; resolution; [4+2] cycloaddition; polycyclic phosphorus heterocycles; P = O reduction; optically active phosphines
Issue Date: 2020
Publisher: MDPI
Citation: "Symmetry", 2020, Vol. 12, nr 3, 346
Abstract: 1-Phenylphosphol-2-ene 1-oxide is effectively resolved by L-menthyl bromoacetate to afford both SP and RP enantiomers of 1-phenylphosphol-2-ene 1-oxide on a multigram scale. The resolved 1-phenylphosphol-2-ene oxide has been found to undergo face-selective and endo-selective cycloadditions with a series of acyclic and cyclic dienes to produce enantiopure P-stereogenic C-P heterocycles of hexahydrophosphindole and hexahydrobenzophosphindole as well as phospha[,6]decene and phospha[,6]undecene structures. Conversions of these cycloadducts to the fully saturated heterocyclic systems as well as to their P (III), P = S, P = Se and P-BH3 derivatives have been demonstrated to occur with retention of configuration and preservation of configurational homogeneity at P. A perplexing case of stereomutation at P during reduction of a tricyclic β-hydroxy phosphine oxide by PhSiH3 at 80 °C has been recorded.
DOI: 10.3390/sym12030346
Appears in Collections:Artykuły naukowe (WNŚiNoZ)

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