Efficient asymmetric synthesis of α-alkylated benzylic methyl sulfonates |
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Authors: | Dieter Enders Wacharee Harnying |
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Institution: | Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Str. 1, 52074 Aachen, Germany |
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Abstract: | The first highly efficient auxiliary-controlled synthesis of various α-substituted sulfonic acid derivatives is described. Alkyl or aryl halides were reacted with lithiated benzylic sulfonic esters bearing 1,2:5,6-di-O-isopropylidene-α-d-allofuranose as a removable enantiopure alcohol auxiliary to give the alkylated products in excellent diastereomeric excesses. The racemization-free cleavage conditions provided highly enantioenriched sulfonic acid derivatives (ee≥98%). |
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Keywords: | Asymmetric synthesis Alkylation Sulfonates Sugar auxiliary |
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