Asymmetric synthesis of alpha-branched primary amines on solid support via novel hydrazine resins |
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Authors: | Enders D Kirchhoff J H Köbberling J Peiffer T H |
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Institution: | Institut für Organische Chemie der Rheinisch-Westf?lischen Technischen Hochschule Aachen, Professor-Pirlet-Strasse 1, D-52074 Aachen, Germany. enders@rwth-aachen.de |
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Abstract: | reaction: see text]. Two novel chiral hydrazine resins for asymmetric solid-phase synthesis have been developed. The enantiopure beta-methoxyamino auxiliaries, derived from trans-4-hydroxy-(S)-proline and (R)-leucine, were attached to Merrifield resin and transformed into their corresponding hydrazines. Immobilization of various aldehydes, followed by 1,2-addition of organolithium reagents to the resulting enantiopure hydrazones and reductive cleavage from the solid support, furnished alpha-branched amines, which were isolated as their corresponding amides in good overall yields and enantiomeric excesses of up to 86%. |
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