title: Synthesis of γ-hydroxypropyl P-chirogenic (±)-phosphorus oxide derivatives by regioselective ring-opening of oxaphospholane 2-oxide precursors.
abstract: The synthesis of P-chirogenic (±)-phosphine oxides and phosphinates via selective nucleophilic ring opening of the corresponding oxaphospholanes is described. Two representative substrates: the phosphonate 2-ethoxy-1,2-oxaphospholane 2-oxide and the phosphinate 2-phenyl-1,2-oxaphospholane 2-oxide were reacted with various Grignard reagents to produce a single alkyl/aryl product. These products may possess further functionalities in addition to the phosphorus center such as the γ-hydroxypropyl group which results from the ring opening and π-donor moieties such as aryl, allyl, propargyl and allene which originates from the Grignard reagent.
authors.affiliation: Department of Organic Chemistry, IIBR-Israel Institute for Biological Research, P.O. Box 19, Ness Ziona, 74100, Israel.
authors.forename: Iris
authors.initials: I
authors.lastname: Binyamin
authors.affiliation: Department of Organic Chemistry, IIBR-Israel Institute for Biological Research, P.O. Box 19, Ness Ziona, 74100, Israel.
authors.forename: Shoval
authors.initials: S
authors.lastname: Meidan-Shani
authors.affiliation: Department of Organic Chemistry, IIBR-Israel Institute for Biological Research, P.O. Box 19, Ness Ziona, 74100, Israel.
authors.forename: Nissan
authors.initials: N
authors.lastname: Ashkenazi
keywords: Grignard reagents; chirogenic phosphorus; oxaphospholanes; phosphinates; phosphine oxides