The preparation of (R)- and (S)-isopropylidene glycerol 1 of high enantiomeric excess (> 98%) was accomplished through salt formation between their hydrogen phthalates with (S)- and (R)-1-methylbenzylamine [MBA] respectively, selective crystallization of these salts and subsequent regeneration of optically active compounds 1 by saponification. The progress of resolution was followed by HPLC analysis on Chiralcel OJ, after converting the hydrogen phthalates into the corresponding mono methyl esters by diazomethane.
Synthesis of (R)- and (S)-isopropylidene glycerol / M. Pallavicini, E. Valoti, L. Villa, O. Piccolo. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 5:1(1994), pp. 5-8. [10.1016/S0957-4166(00)80470-X]
Synthesis of (R)- and (S)-isopropylidene glycerol
M. PallaviciniPrimo
;E. ValotiSecondo
;
1994
Abstract
The preparation of (R)- and (S)-isopropylidene glycerol 1 of high enantiomeric excess (> 98%) was accomplished through salt formation between their hydrogen phthalates with (S)- and (R)-1-methylbenzylamine [MBA] respectively, selective crystallization of these salts and subsequent regeneration of optically active compounds 1 by saponification. The progress of resolution was followed by HPLC analysis on Chiralcel OJ, after converting the hydrogen phthalates into the corresponding mono methyl esters by diazomethane.
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