ChemComm
Communication
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Scheme 1 Asymmetric ring-opening of aniline/water and deprotection
of the methyl ether 3a.
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Scheme 2 Proposed catalytic model.
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In summary, we demonstrated the first direct enantioselective
desymmetrization of meso-aziridines with primary alcohols. The
chiral Mg(II)–N,N0-dioxide complex mediated the asymmetric ring-
opening to generate a variety of optically active b-amino ethers in
good yields (up to 96%) with excellent enantioselectivities (up to
92% ee). The catalytic system can also tolerate the nucleophilic
ring-opening of meso-aziridine with aniline and water, giving
1,2-amino alcohols and 1,2-diamines in excellent enantio-
selectivities, respectively. The application of this catalytic protocol
to other reactions is in progress.
14 For reviews and examples of N,N0-dioxide–metal complexes in asym-
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Chim. Sin., 2014, 72, DOI: 10.6023/A13121253.
We appreciate the National Natural Science Foundation of
China (No. 21321061 and 21172151), and the Ministry of
Education (No. 20110181130014) for financial support.
Notes and references
1 For selected reviews, see: (a) X. E. Hu, Tetrahedron, 2004, 60, 15 See ESI† for details.
2701; (b) A. K. Yudin, Aziridines and Epoxides in Organic Synthesis, 16 Moderate results (53% yield and 72% ee) were obtained using
Wiley-VCH, Weinheim, Germany, 2006.
2 C. Schneider, Angew. Chem., Int. Ed., 2009, 48, 2082.
phenylmethanol. Phenol failed in the reaction.
17 M. V. Bhatt and S. S. El-Morey, Synthesis, 1982, 1048.
3 For selected b-amino alcohols, see: (a) Y. Wang, S. Chackalamannil, 18 V. A. Soloshonok, C. Roussel, O. Kitagawa and A. E. Sorochinsky,
Z. Hu, C. D. Boyle, C. M. Lankin, Y. Xia, R. Xu, T. Asberom, Chem. Soc. Rev., 2012, 41, 4180.
D. Pissarnitski, A. W. Stamford, W. J. Greenlee, J. Skell, S. Kurowski, 19 CCDC 991793 (3b).
6674 | Chem. Commun., 2014, 50, 6672--6674
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