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2005
Protection
O 0345
12- 063
Hexafluoroacetone as a Protecting and Activating Reagent. Regioselective Esterification of Aspartic, Malic, and Thiomalic Acid. — Hexafluoroacetone (II) reacts
selectively with the α-functionalized dicarboxylic acids (I) to give exclusively the
five-membered lactones (III) in excellent yields. With formation of the lactone the
α-functionality is protected while the β-carboxylic groups of (I) remain unaffected and
can be derivatized separately. Esterification of the β-carboxylic group can be achieved
directly or via acid chloride (IV). Acid chloride (IV) reacts with polyalcohols like glycol (V) or pentaerythritol to give the corresponding polyesters, e.g. (VI). Consecutive
aminolysis of the polylactones obtained leads to branched peptides and depsipeptides
or dendrimers. — (PUMPOR, K.; WINDEISEN, E.; SPENGLER, J.; ALBERICIO, F.;
BURGER*, K.; Monatsh. Chem. 135 (2004) 11, 1427-1443; Fachbereich Chem.,
Univ. Leipzig, D-04103 Leipzig, Germany; Eng.) — H. Hoennerscheid
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