Premium
Chiral Phosphine Ligands from Amino Acids. II. A Facile Synthesis of Phosphinoserines by Nucleophilic Phosphination Reactions – X‐Ray Structure Analyses of Ar 2 P–CH 2 –CH(NHBOC)(COOMe) (Ar = Ph, m ‐xylyl)
Author(s) -
Brauer David J.,
Kottsieper Konstantin W.,
Schenk Stefan,
Stelzer Othmar
Publication year - 2001
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/1521-3749(200106)627:6<1151::aid-zaac1151>3.0.co;2-8
Subject(s) - chemistry , nucleophile , phosphine , stereochemistry , medicinal chemistry , enantiomer , catalysis , organic chemistry
Phosphino derivatives of serine R 2 P–CH 2 –CH(NHBOC)(COOMe) ( 2 a – 2 d ) have been obtained in high yield by nucleophilic phosphination of N‐( tert .butoxycarbonyl)‐3‐iodo‐L‐alanine methylester with secondary phosphines R 2 PH (R = Ph, 2‐tolyl, 3,5‐xylyl, cyclohexyl) in DMF using potassium carbonate as the base. Deprotection of 2 b with HCl affords the amino acid ester hydrochloride [2‐Tol 2 P–CH 2 –CH(NH 3 )(COOMe)] + Cl – ( 3 a ). The X‐ray structures of 2 a (space group P2 1 /n) and 2 c (space group P 1) have been determined. The two enantiomers of 2 a or 2 c are interconnected by N–H…O hydrogen bridges forming dimers in the solid state.