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Dimethylzinc‐Mediated, Enantioselective Synthesis of Propargylic Amines
Author(s) -
Zani Lorenzo,
Eichhorn Torsten,
Bolm Carsten
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601347
Subject(s) - dimethylzinc , enantiopure drug , enantioselective synthesis , reagent , chemistry , enantiomer , organic chemistry , stoichiometry , aryl , alkynylation , enantiomeric excess , combinatorial chemistry , catalysis , alkyl
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 β‐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.