189749-01-7Relevant academic research and scientific papers
A systematic synthetic approach to phosphinophenyl-glycine and -alanine. Chiral phosphine ligands with amino acid moieties
Tepper, Michael,Stelzer, Othmar,Haeusler, Thomas,Sheldrick, William S.
, p. 2257 - 2258 (1997)
Ortho- and para-phosphinophenyl derivatives of glycine and alanine have been synthesised by nucleophilic phosphination of 2- and 4-fluorophenylglycine and -alanine with Ph(R)PK (R = Me, Ph). The structure of 2-diphenylphosphino-α-phenylglycine has been id
Water soluble phosphines: Part XIII. Chiral phosphine ligands with amino acid moieties
Brauer, David J.,Schenk, Stefan,Ro?enbach, Stefan,Tepper, Michael,Stelzer, Othmar,H?usler, Thomas,Sheldrick, William S.
, p. 116 - 126 (2000)
Nucleophilic phosphination of the potassium or sodium salt of the fluorophenylalanines (1a, 2a) or -glycines (3a, 4a) with potassium phosphides Ph(R)PK (R=Me, Ph) yields chiral phosphine ligands (1-7) with amino acid moieties. The X-ray structure of 3·2H2O (space group Pbca) has been determined showing a betaine type structure for the amino acid moiety. The α-methyl derivatives of the phosphinophenylglycines (10, 11) were obtained in an analogous manner as 1-7. ortho- and para-Fluoroacetophenones have been employed as starting material for the syntheses of α-[4-fluorophenyl]-α-methylglycine (9c) and its ortho-isomer (8c), the X-ray structure of its monohydrate has been determined (space group P1?). The N-acetyl (3b, 8e) and ester derivatives (3d, 8d) of 3 and 8c are accessible using standard procedures. Resolution of the diastereomeric salt 12 obtained from (S)-(+)-2-hydroxymethylpyrrolidine and racem-8e by fractionated crystallization yielded the (S,R)-isomer. The absolute configuration of (S,R)-12 was determined by X-ray structural analysis (space group P212121). Cleavage of (S,R)-12 with hydrochloric acid gave enantiopure (R)-8e [α]D20=-30.9° (c=1, CH3OH).
