Enantioselective ring-opening reactions of racemic ethynyl epoxides via copper-allenylidene intermediates: efficient approach to chiral beta-amino alcohols.

Abstract

Enantioselective copper-catalyzed ring-opening reactions of racemic ethynyl epoxides with amines using (R)-DTBM-MeO-BIPHEP as a chiral ligand have been found to give the corresponding amino alcohols in high yields with up to 94% ee. The reaction is considered to proceed via copper-allenylidene complexes as key intermediates. This methodology may provide a novel synthetic approach to optically active amino alcohols, the structures of which are widely found in many natural products, biologically active compounds, and chiral ligands.

DOI: 10.1021/jo901064n

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Cite this paper

@article{Hattori2009EnantioselectiveRR, title={Enantioselective ring-opening reactions of racemic ethynyl epoxides via copper-allenylidene intermediates: efficient approach to chiral beta-amino alcohols.}, author={Gaku Hattori and Akiko Yoshida and Yoshihiro Miyake and Yoshiaki Nishibayashi}, journal={The Journal of organic chemistry}, year={2009}, volume={74 20}, pages={7603-7} }