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Synfacts 2011(3): 0279-0279  
DOI: 10.1055/s-0030-1259502
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Opening of meso-Epoxides with Aromatic and Aliphatic Amines

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
H. Bao, J. Wu, H. Li, Z. Wang, T. You, K. Ding*
Shanghai Institute of Organic Chemistry and University of Science and Technology of China, Hefei, P. R. of China
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Publikationsdatum:
16. Februar 2011 (online)

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Significance

Asymmetric ring-opening of epoxides with amines is a convenient route to enantiomerically enriched β-amino alcohols. However, few catalytic methods for this transformation afford high ee values with aliphatic amines. In this paper, decent enantioselectivities were obtained using Mg complexes of BINOL derivatives for epoxide ring opening with both aromatic (55-92% yields, 65-82% ee) and aliphatic (46-92% yields, 47-94% ee) amines as nucleophiles. The easy availability of the catalytic system without the need to prepare structurally complex ligands is one of the important advantages of this system.