128014-11-9Relevant academic research and scientific papers
Stereoselective addition of grignard reagents to new P-chirogenic N-phosphinoylbenzaldimines: Effect of the phosphorus substituents on the stereoselectivity
Notar Francesco, Irene,Egloff, Coraline,Wagner, Alain,Colobert, Francoise
, p. 4037 - 4045 (2011/09/15)
Several phosphinoylimines have been synthesized in five steps by starting from the appropriate phosphane oxide and were then treated with methylmagnesium bromide to give both diastereoisomers in high yields and with promising diastereomeric ratios. Then N-[(tert-butyl)(phenyl)phosphinoyl]benzaldimine, which displayed the best results, was subjected to the 1,2-addition of various Grignard reagents to evaluate the best chiral induction due to the stereogenic phosphorus atom. The corresponding adducts were obtained in excellent yields and with moderate to excellent diastereoisomeric ratios. Copyright
Reaction of metallated tert-butyl(phenyl)phosphane oxide with electrophiles as a route to functionalized tertiary phosphane oxides: Alkylation reactions
Haynes, Richard K.,Au-Yeung, Tin-Lok,Chan, Wai-Kuen,Lam, Wai-Lun,Li, Zhi-Yi,Yeung, Lam-Lung,Chan, Albert S. C.,Li, Pauline,Koen, Mark,Mitchell, Craig R.,Vonwiller, Simone C.
, p. 3205 - 3216 (2007/10/03)
P-Chiral tertiary phosphane oxides have been prepared from each of the secondary phosphane oxides racemic 1, (S(p))-(-)-4 and (Rp)-(+)-tert-butylphenylphosphane oxide (5) by lithiation with LDA or nBuLi, or sodiation with sodium hydride, in THF, and then by treatment with a series of primary alkyl halides. Doubly P-chiral ditertiary bis(phosphane oxides) are also obtained from these metallated secondary phosphane oxides by treatment with electrophiles based on straight-chain, tartrate-derived, and bishalomethylarene dihalides. In general, the bis-phosphane oxides are obtained in good yields. However, when the α,ω-dihalide bears an embedded heteroatom (O or Si), yields are diminished. The enantiomeric purity of each of the products was assessed through admixture with (R(p))- and (S(p))-tert-butyl(phenyl)phosphanylthioic acids and measurement of the tert-butyl resonances in the 1H-NMR spectra. In all cases, the act of metallation of the enantiomerically pure secondary phosphane oxide followed by its alkylation is not accompanied by detectable racemization. This method for preparing P-chiral tertiary phosphane oxides is therefore more straightforward than those described previously.
Reaction of Thiolo and Selenolo Esters of Phosphorus Acids with Halogens. Part 2. Interaction of S-Methyl t-Butyl(phenyl)- and Di-t-butyl-phosphinothiolates with Elemental Bromine and Iodine
Krawiecka, Bozena,Wojna-Tadeusiak, Elzbieta
, p. 301 - 309 (2007/10/02)
The reaction of S-methyl t-butyl(phenyl)- and di-t-butyl-phosphinothiolates with bromine and iodine involves the transient formation of the same type of halosulphonium salts, ButRP(O)S+(X)MeX- and phosphonium salts, Busup
