Demchuk, Oleg M.Pietrusiewicz, Kazimierz MichałKoprowski, MarekDrzazga, ZbigniewParcheta, RenataŁastawiecka, ElżbietaJustyniak, Iwona2022-06-222022-06-222020"Symmetry", 2020, Vol. 12, nr 3, 346http://hdl.handle.net/20.500.12153/32231-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[5.2.1.02,6]decene and phospha[5.2.2.02,6]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.enUznanie autorstwa-Użycie niekomercyjne-Bez utworów zależnych 3.0 Polskahttp://creativecommons.org/licenses/by-nc-nd/3.0/pl/P-stereogenicity1-phenylphosphol-2-ene 1-oxideresolution[4+2] cycloadditionpolycyclic phosphorus heterocyclesP = O reductionoptically active phosphinesinfo:eu-repo/semantics/article10.3390/sym12030346