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Addition von Dialkylphosphiten und Dialkyl(trimethylsilyl)phosphiten an 2‐(Benzyloxy)propanal Darstellung aller vier stereoisomeren (1,2‐Dihydroxy‐[1‐ 2 H 1 ]propyl)phosphonsäuren aus chiralen Lactaten
Author(s) -
Hammerschmidt Friedrich
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910185
Subject(s) - chemistry , diastereomer , trimethylsilyl , diisopropyl ether , trimethyl phosphite , organic chemistry , medicinal chemistry , catalysis
Addition of Dialkyl Phosphites and Dialkyl Trimethylsilyl Phosphites to 2‐(Benzyloxy)propanal – Preparation of all Four Stereoisomeric (1,2‐Dihydroxy‐[1‐ 2 H 1 ]propyl)phosphonic Acids from Chiral Lactates Dimethyl trimethylsilyl phosphite, diisopropyl trimethylsilyl phosphite, dimethyl phosphite, and diisopropyl phosphite were added to 2‐(benzyloxy)propanals 4 and 6 at different temperatures in THF and CH 2 Cl 2 . The ratio of diastereomers formed was highest for diisopropyl trimethylsilyl phosphite ( erythro/threo 3:1) and dropped to about 1:1 for diisopropyl phosphite. Starting from chiral lactates all four stereoisomeric diisopropyl (2‐benzyloxy‐1‐hydroxy‐[1‐ 2 H 1 ]phosphonates were prepared and deprotected. The (1,2‐dihydroxy‐[1‐ 2 H 1 ]propyl)phosphonic acids formed were purified as cyclohexylammonium salts. The relative configuration of phosphonic acid of (−)‐ 11 was determined by comparison with the salt (1 R ,2 R )‐ 12 derived from fosfomycin.