Addition von Dialkylphosphiten und Dialkyl(trimethylsilyl)phosphiten an 2-(Benzyloxy)propanal Darstellung aller vier stereoisomeren (1,2-Dihydroxy-[1-2H1]propyl)phosphonsäuren aus chiralen Lactaten
✍ Scribed by Hammerschmidt, Friedrich
- Book ID
- 102903145
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- English
- Weight
- 814 KB
- Volume
- 1991
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
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.