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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Diastereoselective synthesis of 2-aminoalkyl-3-sulfonyl-1,3-oxazolidines on solid support
Kilian Conde-Frieboes1, Rie K Schjeltved, Jens Breinholt
1Novo Nordisk A/S, Discovery Chemistry, Novo Nordisk Park, DK-2760 Måløv, Denmark.
Abstract:
Herein we report our investigation on the oxidation of solid-support-bound amino alcohols to their corresponding aldehydes. These aldehydes were converted into diastereomerically pure (>10:1) 2,4-cis-2-aminoalkyl-3-sulfonyl-1,3-oxazolidines using optically pure 1,2-amino alcohols. The relative configuration was determined using the nuclear Overhauser effect (NOE). The synthesized oxazolidines, which were obtained in high purities, represent a new, diverse scaffold for the solid-phase synthesis of libraries directed toward a pharmacological target.
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