31253-31-3

Upstream product

• 254100-63-5 C₂₆H₄₆NO₃PSSi 
• 1068-55-9 isopropylmagnesium chloride 
• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 36050-92-7 iso-propyl methyl phenylphosphine 
• 6372-43-6 diisopropylphenylphosphane 
• 17586-69-5 Methyl-diisopropyl-phenyl-phosphonium Iodid 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Experimental and theoretical investigations of the stereoselective synthesis of P-stereogenic phosphine oxides

An efficient enantioselective strategy for the synthesis of variously substituted phosphine oxides has been developed, incorporating the use of (1S,2S)-2-aminocyclohexanol as the chiral auxiliary. The method relies on three key steps: 1) Highly diastereoselective formation of PV oxazaphospholidine, rationalized by a theoretical study; 2) highly diastereoselective ring-opening of the oxazaphospholidine oxide with organometallic reagents that takes place with inversion of configuration at the P atom; 3) enantioselective synthesis of phosphine oxides by cleavage of the remaining P-O bond. Interestingly, the use of a PIII phosphine precursor afforded a P-epimer oxazaphospholidine. Hence, the two enantiomeric phosphine oxides can be synthesized starting from either a PV or a PIII phosphine precursor, which constitutes a clear advantage for the stereoselective synthesis of sterically hindered phosphine oxides. That's handy: An efficient enantioselective strategy for the synthesis of variously substituted phosphine oxides was developed, incorporating the use of (1S,2S)-2-aminocyclohexanol as a chiral auxiliary, whereby enantiomeric phosphine oxides can be synthesized starting from either a PV or a PIII phosphine precursor.

A simple resolution procedure using the Staudinger reaction for the preparation of P-stereogenic phosphine oxides

The resolution of a variety of (±)-P-stereogenic phosphines is achieved by exploiting the Staudinger reaction of a (±)-phosphine with enantiopure (1S,2R)-O-(tert-butyldimethylsilyl)isobornyl-10-sulfonyl azide. The resulting mixtures of diastereomeric phosphinimines are generally separable by fractional crystallization or flash chromatography. Subsequent acid-catalyzed hydrolysis provides the corresponding optically pure phosphine oxides in high yields.

A Novel Resolution Procedure for the Preparation of P-Stereogenic Phosphine Oxides

(Matrix Presented) A new general route for preparing enantiomerically pure P-stereogenic phosphine oxides has been developed by exploiting the Staudinger reaction between racemic tertiary phosphines and an enantiomerically pure organoazide. The resulting

Synthesis of P-chiral, non-racemic phosphinylacetates via enzymatic resolution of racemates

A series of racemic methyl phosphinylacetates was hydrolyzed in the presence of porcine liver esterase (PLE) under the kinetic resolution conditions to give the corresponding P-chiral phosphinylacetic acids and recovered esters in high enantiomeric purity (72-100% ee). The Jones' active site model was applied to explain the enantioselectivity of this reaction.