Liebigs Annalen der Chemie

Enantioselektive Verseifungen substituierter, achiraler 3??Acyloxy??propylester mit Lipasen: Herstellung chiraler Derivate von „Tris (hydroxymethyl) methan”

J Ehrler, D Seebach

Index: Ehrler, Juerg; Seebach, Dieter Liebigs Annalen der Chemie, 1990 , # 4 p. 379 - 388

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Citation Number: 32

Abstract

Both OH groups of 11 were acylated (ethanoyl-, propanoyl-, butanoyl, hexanoyl, and octanoyl derivatives 6a-e), and the formed triesters were partially hydrolyzed by lipases. According to" F-NMR analysis of the corresponding Mosher ersters, the monocapronate 12d formed by PPL (porcine pancreas li-pase) showed an enantiomeric ratio of 93.5: 6.5 (87% ee). Using standard reactions, it was converted into chiral non-racemic derivatives 16 (0- ...