A Short Synthesis of L-Acosamine Based on Nitroaldol Addition (Henry Reaction). Analysis of the Key Step Concerning Solvent and Temperature Effects

A Menzel, R Öhrlein, H Griesser, V Wehner…

Index: Menzel, Andreas; Oehrlein, Reinhold; Griesser, Helmut; Wehner, Volkmar; Jaeger, Volker Synthesis, 1999 , # 9 p. 1691 - 1702

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Citation Number: 10

Abstract

Abstract: Of several routes explored for the synthesis of 3-amino-2, 3, 6-trideoxyhexoses such as L-acosamine (L-arabino), two versions of the nitroaldol strategy were completed. The silyl nitronate approach with use of" anhydrous" tetrabutylammonium fluoride (Bu4NF) turned out to be rather complex, since the key step led to a moderately diastereoselective, though still efficient solution. In a simpler mode, with Bu4NF trihydrate as a catalyst, the ...