249931-33-7Relevant academic research and scientific papers
New procedures for the resolution of chiral tert-butylphenylphosphine oxide and some of its reactions
Drabowicz, Joezef,Lyzwa, Piotr,Omelanczuk, Jan,Pietrusiewicz, K. Michal,Mikolajczyk, Marian
, p. 2757 - 2763 (1999)
Racemic t-butylphenylphosphine oxide was resolved via formation of diastereoisomeric complexes with (+)-(R)-1,1'-binaphthalene-2,2'-diol and (+)-(S)-mandelic acid. With the latter complexing agent, separation of the essentially enantiopure (-)-(S)-enantio
Stereospecific Synthesis of α- And β-Hydroxyalkyl P-Stereogenic Phosphine-Boranes and Functionalized Derivatives: Evidence of the P=O Activation in the BH3-Mediated Reduction
Lemouzy, Sébastien,Nguyen, Duc Hanh,Camy, Valentine,Jean, Marion,Gatineau, David,Giordano, Laurent,Naubron, Jean-Valère,Vanthuyne, Nicolas,Hérault, Damien,Buono, Gérard
supporting information, p. 15607 - 15621 (2015/11/03)
Access to hydroxy-functionalized P-chiral phosphine-boranes has become an important field in the synthesis of P-stereogenic compounds used as ligands in asymmetric catalysis. A family of optically pure α and β-hydroxyalkyl tertiary phosphine-boranes has been prepared by using a three-step procedure from readily accessible enantiopure adamantylphosphinate, obtained by semi-preparative HPLC on multigram scale. Firstly, a two-step one-pot transformation affords the enantiopure hydroxyalkyl tertiary phosphine oxides in good yields and enantioselectivities. The third step, BH3-mediated reduction, allows the formation of the desired phosphine-boranes with excellent stereospecifity. The mechanistic study of this reduction provides new evidence to elucidate the crucial role of the pendant hydroxy group and the subsequent activation of the P=O bond by the boron atom.
Lipase-mediated stereoselective transformations of chiral organophosphorus P-boranes revisited: Revision of the absolute configuration of alkoxy(hydroxymethyl)phenylphosphine P-boranes
Kwiatkowska, Malgorzata,Krasinski, Grzegorz,Cypryk, Marek,Cierpial, Tomasz,Kielbasinski, Piotr
experimental part, p. 1581 - 1590 (2011/12/15)
The lipase-promoted kinetic resolution of a series of alkoxy(hydroxymethyl) phenylphosphine P-boranes proceeded with moderate stereoselectivity to give both the unreacted substrates and their O-acetyl derivatives. The absolute configurations of the produc
Lipase-catalyzed kinetic resolution of P-chiral phosphorus compounds: Enantiopreference of Pseudomonas lipase and Candida antarctica lipase
Shioji, Kosei,Ueno, Yuichiro,Kurauchi, Yoshimitsu,Okuma, Kentaro
, p. 6569 - 6571 (2007/10/03)
Optically active 1-hydroxymethylalkylphenylphosphine oxides 1a-c were prepared by Pseudomonas fluorescens lipase (lipase AK) and Candida antarctica lipase (CAL)-catalyzed optical resolution. Lipase AK-catalyzed resolution of tert-butyl derivative 1c showed R-selectivity, whereas CAL preferred the S-enantiomer.
