Dimethylzinc-mediated, enantioselective synthesis of propargylic amines |
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Authors: | Zani Lorenzo Eichhorn Torsten Bolm Carsten |
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Institution: | Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany. |
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Abstract: | A one-pot, enantioselective synthesis of N-aryl propargylic amines, using alkynylation reagents obtained from dimethylzinc and terminal acetylenes in combination with various aldehydes and o-methoxyaniline as starting materials, has been developed. Enantiopure beta-amino alcohols derived from norephedrine were used as non-covalent chiral auxiliaries, both in stoichiometric or substoichiometric amount. After optimization, propargylic amines were obtained in good to high yields (up to 93%) and with moderate to high enantiomeric excesses (up to 97% ee). The possibility to recover the chiral auxiliary after the reaction was demonstrated. |
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Keywords: | alkynes amino alcohols C?C bond formation enantioselective synthesis organozinc chemistry |
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