211565-44-5

Upstream product

• 87214-07-1 (2R,4S,5R)-2,3,4,5-tetrahydro-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphosphole 
• 644-97-3 Dichlorophenylphosphine 
• 20663-35-8 (S_p)-(2-methoxyphenyl)methylphenylphosphine oxide 
• 77929-22-7 (R)-(-)-[O-methyl (o-anisyl)phenylphosphinate] 
• 35143-99-8 (R_p)-(2-methoxyphenyl)methylphenylphosphine oxide 
• 321-98-2 (1S,2R)-(+)-ephedrine 
• 299-42-3 ephedrine 
• 6143-71-1 bis(dimethylamino)phenyl phosphine 

Downstream Products

• 130818-07-4 (S_P)-(-)-N-<(1S,2R)-2-Hydroxy-1-methyl-2-phenylethyl>-N-methyl-P-(2-methoxyphenyl)-P-phenylphosphinamide 
• 35143-99-8 (R_p)-(2-methoxyphenyl)methylphenylphosphine oxide 
• 130856-88-1 (R)-ethyl(2-methoxyphenyl)(phenyl)phosphane oxide 
• 77929-22-7 (R)-(-)-[O-methyl (o-anisyl)phenylphosphinate] 
• 130818-09-6 (S)-(2-methoxyphenyl)(4-methoxyphenyl)(phenyl)phosphine oxide 
• 130818-08-5 bis-(phenyl-2-methoxyphenyl)-pyrophosphinate 
• 20663-35-8 (S_p)-(2-methoxyphenyl)methylphenylphosphine oxide 
• 87214-07-1 (2R,4S,5R)-2,3,4,5-tetrahydro-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphosphole 

Relevant academic research and scientific papers

THE NUCLEOPHILIC DISPLACEMENT ROUTE TO HOMOCHIRAL ARYLPHOSPHINE OXIDES

The stereoisomerically pure oxazaphospholidine formed by reaction of (1R,2S)-ephedrine with PhPCl2 is oxidised by ButOOH to the corresponding P-oxide, shown to have R-stereochemistry at phosphorus by X-ray analysis.The product reacts regio- and stereospecifically with o-anisylmagnesium bromide to give the product formed by P-O fission with retention of configuration, which was also characterised by X-ray diffraction.The ephedrine residue was replaced by O-methyl under acid catalysis with inversion of configuration.Attempts to incorporate p-fluorophenyl using similar conditions led to isolation of the pyrophosphinate in low yield.The OMe residue in the methoxyphosphinate was readily displaced by aliphatic or aromatic Grignard reagents giving the corresponding phosphine oxides with inversion of configuration.This procedure constitutes a simple route to di- and triarylphosphine oxides in ca. 95percent e.e.; optical purities were estimated by NMR methods.

Asymmetric Synthesis of 2-Organo-1,3,2-oxazaphospholidines

Achiral organophosphonous diamides RP(NMe2)2 react with chiral amino alcohols such as L-ephedrine and L-prolinol to form methyl- and phenyl-substituted mono- (2,3) and bicyclic 1,3,2-oxazaphospholidines (6-8) in good yields.Organophosphonous dichloride allow the synthesis of oxazaphospholidines only for R = tert-butyl (4,5).The diastereomeric excess of the ephedrine and prolinol derivatives ranges from 80percent (R = methyl) to 95percent d.e. (R = tert-butyl).The bis-1,3,2-oxazaphospholidine 8, made from two mols of prolinol and one mol of 1,2-ethanediylbis, is virtually diastereomerically pure according to the NMR spectrum.Analysis of the 13C-31P and 1H-31P coupling constants afford the structural assignment of the ephedrine derivatives as (2S,4S,5R) and the prolinol derivatives as (2R,5S).