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Letter

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

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Stéphane Azoulay, Kei Manabe, and Shū 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

Org. Lett., 2005, 7 (21), pp 4593–4595

DOI: 10.1021/ol051546z

Publication Date (Web): September 14, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, skobayas@mol.f.u-tokyo.ac.jp

Abstract

An operationally simple and environmentally benign protocol for the catalytic asymmetric ring opening of meso-epoxides with aromatic amines has been developed. The reactions proceeded smoothly in the presence of 1 mol % of Sc(OSO₃C₁₂H₂₅)₃ and 1.2 mol % of a chiral bipyridine ligand in water to afford β-amino alcohols in high yields with excellent enantioselectivities.

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Published In Issue October 13, 2005
Received June 30, 2005

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Letter

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

Abstract

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Related Content

Asymmetric Catalysis of Epoxide Ring-Opening Reactions

Highly Chemoselective Addition of Amines to Epoxides in Water

Catalytic Asymmetric Hydroxymethylation of Silicon Enolates Using an Aqueous Solution of Formaldehyde with a Chiral Scandium Complex

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