Catalytic Asymmetric Ring Opening of meso-Epoxides with Aromatic Amines in Water

Stéphane Azoulay, Kei Manabe and Shu Kobayashi*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: skobayasmol.f.u-tokyo.ac.jp

S. Azoulay, K. Manabe, S. Kobayashi, Org. Lett., 2005, 7, 4593-4595.

DOI: 10.1021/ol051546z (free Supporting Information)

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Abstract

Sc(OSO₃C₁₂H₂₅)₃ catalyses the asymmetric ring opening of meso-epoxides with aromatic amines in the presence of 1.2 mol-% of a chiral bipyridine ligand to afford β-amino alcohols in high yields with excellent enantioselectivities using water as environmentally benign solvent.

see article for more reactions

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Key Words

β-amino alcohols

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ID: J54-Y2005-1660