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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

 

作者: Friedrich Hammerschmidt,  

 

期刊: Liebigs Annalen der Chemie  (WILEY Available online 1991)
卷期: Volume 1991, issue 5  

页码: 469-475

 

ISSN:0170-2041

 

年代: 1991

 

DOI:10.1002/jlac.199119910185

 

出版商: WILEY‐VCH Verlag

 

关键词: Propanal, 2‐benzyloxy‐;Phosphites, dialkyl trimethylsilyl;Phosphonates, α‐hydroxypropyl, α‐(trimethylsiloxy)propyl‐;Phosphonic acids, (1,2‐dihydroxy[1‐2H1]propyl)‐

 

数据来源: WILEY

 

摘要:

Addition of Dialkyl Phosphites and Dialkyl Trimethylsilyl Phosphites to 2‐(Benzyloxy)propanal – Preparation of all Four Stereoisomeric (1,2‐Dihydroxy‐[1‐2H1]propyl)phosphonic Acids from Chiral LactatesDimethyl trimethylsilyl phosphite, diisopropyl trimethylsilyl phosphite, dimethyl phosphite, and diisopropyl phosphite were added to 2‐(benzyloxy)propanals4and6at different temperatures in THF and CH2Cl2. The ratio of diastereomers formed was highest for diisopropyl trimethylsilyl phosphite (erythro/threo3:1) and dropped to about 1:1 for diisopropyl phosphite. Starting from chiral lactates all four stereoisomeric diisopropyl (2‐benzyloxy‐1‐hydroxy‐[1‐2H1]phosphonates were prepared and deprotected. The (1,2‐dihydroxy‐[1‐2H1]propyl)phosphonic acids formed were purified as cyclohexylammonium salts. The relative configuration of phosphonic acid of (−)‐11was determined by comparison with the salt (1

 

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