Several biologically active compounds structurally include the enantiopure 2-substituted-1,4-benzodioxane scaffold. The straightforward racemization that affects reactions involving most of the common chemical reactives is thus a crucial issue. The developing of a completely stereo-controlled synthetic route that does not affect the enantiomeric excess is consequently mandatory. It is also important to set up a reliable chiral HPLC method, able to follow the reaction, and to improve the synthetic performances. Here, we report the chiral investigation of two different synthons, we specifically evaluated the synthetic pathways that could be run in order to afford them, avoiding the racemization processes, which could normally occur in basic conditions. In addition, we developed peculiar chiral HPLC methods in order to resolve the enantiomers, define the enantiomeric excess, and fully characterize these compounds.

How do reaction conditions affect the enantiopure synthesis of 2-substituted-1,4-benzodioxane derivatives? / V. Straniero, A. Casiraghi, L. Fumagalli, E. Valoti. - In: CHIRALITY. - ISSN 0899-0042. - 30:7(2018 Jul), pp. 943-950. [10.1002/chir.22968]

How do reaction conditions affect the enantiopure synthesis of 2-substituted-1,4-benzodioxane derivatives?

Straniero, Valentina;Casiraghi, Andrea;Fumagalli, Laura;Valoti, Ermanno
2018-07

Abstract

Several biologically active compounds structurally include the enantiopure 2-substituted-1,4-benzodioxane scaffold. The straightforward racemization that affects reactions involving most of the common chemical reactives is thus a crucial issue. The developing of a completely stereo-controlled synthetic route that does not affect the enantiomeric excess is consequently mandatory. It is also important to set up a reliable chiral HPLC method, able to follow the reaction, and to improve the synthetic performances. Here, we report the chiral investigation of two different synthons, we specifically evaluated the synthetic pathways that could be run in order to afford them, avoiding the racemization processes, which could normally occur in basic conditions. In addition, we developed peculiar chiral HPLC methods in order to resolve the enantiomers, define the enantiomeric excess, and fully characterize these compounds.
1,4-benzodioxane; enantiopure Weinreb amide; enantioselective reaction; enantioseparation; racemate DSC analysis; Analytical Chemistry; Catalysis; Pharmacology; Drug Discovery; 3003; Pharmaceutical Science; Spectroscopy; Organic Chemistry
Settore CHIM/08 - Chimica Farmaceutica
Settore CHIM/06 - Chimica Organica
CHIRALITY
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/582835
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