Efficient Oxidative Resolution of 1-Phenylphosphol-2-Ene and Diels–Alder Synthesis of Enantiopure Bicyclic and Tricyclic P-Stereogenic C-P Heterocycles

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dc.contributor.authorDemchuk, Oleg M.
dc.contributor.authorPietrusiewicz, Kazimierz Michał
dc.contributor.authorKoprowski, Marek
dc.contributor.authorDrzazga, Zbigniew
dc.contributor.authorParcheta, Renata
dc.contributor.authorŁastawiecka, Elżbieta
dc.contributor.authorJustyniak, Iwona
dc.date.accessioned2022-06-22T13:18:06Z
dc.date.available2022-06-22T13:18:06Z
dc.date.issued2020
dc.description.abstract1-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.pl
dc.identifier.citation"Symmetry", 2020, Vol. 12, nr 3, 346pl
dc.identifier.doi10.3390/sym12030346
dc.identifier.urihttp://hdl.handle.net/20.500.12153/3223
dc.language.isoenpl
dc.publisherMDPIpl
dc.rightsUznanie autorstwa-Użycie niekomercyjne-Bez utworów zależnych 3.0 Polska*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/pl/*
dc.subjectP-stereogenicitypl
dc.subject1-phenylphosphol-2-ene 1-oxidepl
dc.subjectresolutionpl
dc.subject[4+2] cycloadditionpl
dc.subjectpolycyclic phosphorus heterocyclespl
dc.subjectP = O reductionpl
dc.subjectoptically active phosphinespl
dc.titleEfficient Oxidative Resolution of 1-Phenylphosphol-2-Ene and Diels–Alder Synthesis of Enantiopure Bicyclic and Tricyclic P-Stereogenic C-P Heterocyclespl
dc.typeinfo:eu-repo/semantics/articlepl
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