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Synthesis of Enantiomeric Dimethyl (1,2,3,4‐Tetrahydroxybutyl)phosphonates
Author(s) -
Wróblewski Andrzej E.
Publication year - 1986
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.198619861105
Subject(s) - chemistry , triethylamine , phosphonate , enantiomer , stereochemistry , aldose , asymmetric induction , erythritol , absolute configuration , organic chemistry , medicinal chemistry , catalysis , enantioselective synthesis , glycoside , food science
A 1 : 1 mixture of (1 S )‐ and (1 R )‐2,4‐ O ‐benzylidene‐1‐ C ‐(dimethoxyphosphoryl)‐D‐erythritol ( 7 and 8 ) and on the other hand a 1 : 9 mixture of (1 S )‐ and (1 R )‐2,4‐ O ‐benzylidene‐1‐ C ‐(dimethoxyphosphoryl)‐D‐threitol ( 13 and 14 ) are obtained in the triethylamine‐catalysed additions of dimethyl phosphonate to 2,4‐ O ‐benzylidene derivatives 2 and 3 of D‐erythrose, and D‐threose, respectively. The absolute configurations at C‐1 in these phosphonates were established by the 1 H NMR spectra of the respective tetraacetates. A model for the 1,3‐asymmetric induction in the Abramov reaction is discussed.