142185-06-6

Upstream product

• 644-97-3 Dichlorophenylphosphine 
• 4073-31-8 (diethylamino)phenylchlorophosphine 
• 1421840-48-3 (S)-4-chloro-2-[(1R)-1-{[(4-methylphenyl)sulfonyl]amino}ethyl]phenylmesityl(phenyl)phosphinate 
• 142087-69-2 P-phenyl-P-2,4,6-trimethylphenylphosphinic acid 
• 142087-74-9 (1R)-N-(1-phenylethyl)-(R_P)-P-phenyl-P-(2,4,6-trimethylphenyl) phosphinamide 

Relevant academic research and scientific papers

Efficient asymmetric synthesis of structurally diverse p-stereogenic phosphinamides for catalyst design

The use of chiral phosphinamides is relatively unexplored because of the lack of a general method for the synthesis. Reported herein is the development of a general, efficient, and highly enantioselective method for the synthesis of structurally diverse P-stereogenic phosphinamides. The method relies on nucleophilic substitution of a chiral phosphinate derived from the versatile chiral phosphinyl transfer agent 1,3,2-benzoxazaphosphinine-2-oxide. These chiral phosphinamides were utilized for the first synthesis of readily tunable P-stereogenic Lewis base organocatalysts, which were used successfully for highly enantioselective catalysis.

The Synthesis of Optically Active P-Phenyl-P-(2,4,6-trimethylphenyl)phosphinamide and an X-Ray Structure of (-)-(1R)-N-(1-Phenylethyl)-(SP)-P-phenyl-P-(2,4,6-trimethylphenyl)phosphinamide

The primary phosphinic amide P-phenyl-P-(2,4,6-trimethylphenyl)phosphinamide has been prepared in optically active form (75percent enantiomeric excess) in six steps from dichlorophenylphosphine.The configuration of the intermediate N-(1-phenylethyl)-P-phenyl-P-(2,4,6-trimethylphenyl)phosphinamide has been established by an X-ray crystal structure determination of the minor diastereoisomer.This compound exhibits in the solid state two independent rotameric conformations about the P-N bond.Geometry optimisation by MNDO MO calculations refined these to the same rotamer having the nitrogen lone pair anticlinal to the P-O bond.