| D3715 | (1R,2R)-N,N'-Dihydroxy-N,N'-bis(diphenylacetyl)cyclohexane-1,2-diamine (1a) |
100mg |
| D3716 | (1S,2S)-N,N'-Dihydroxy-N,N'-bis(diphenylacetyl)cyclohexane-1,2-diamine (1b) |
100mg |
| D3719 | (1R,2R)-N,N'-Dihydroxy-N,N'-bis(3,3,3-triphenylpropionyl)cyclohexane-1,2-diamine (2a) |
100mg |
| D3720 | (1S,2S)-N,N'-Dihydroxy-N,N'-bis(3,3,3-triphenylpropionyl)cyclohexane-1,2-diamine (2b) |
100mg |
Chiral bishydroxamic acids (CBHA) 1 and 2 are ligands used for asymmetric oxidation developed by Yamamoto and his group. For example, a complex with vanadium is used to catalyze the asymmetric epoxidation of allylic alcohols and homoallylic alcohols,1a-c) while a complex with molybdenum is used to catalyze the asymmetric epoxidation of olefins1d) and asymmetric oxidation of sulfides.1e) Asymmetric oxidation reactions using ligands 1 and 2 proceed with high stereoselectivity and can be applied to a wide range of substrates. Application to an industrial-scale synthesis would be expected because the reaction has the following benefits: (1) no dehydration agents are required; (2) the work-up procedure is simple; (3) and the reaction proceeds at 0 dgreeC to room temperature.
References
a) A. U. Barlan, W. Zhang, H. Yamamoto, Tetrahedron 2007, 63, 6075[DOI]. b) W. Zhang, A. Basak, Y. Kosugi, Y. Hoshino, H. Yamamoto, Angew. Chem. Int. Ed. 2005, 44, 4389[DOI]. c) W. Zhang, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 286[DOI]. d) A. U. Barlan, A. Basak, H. Yamamoto, Angew. Chem. Int. Ed. 2006, 45, 5849[DOI]. e) A. Basak, A. U. Barlan, H. Yamamoto, Tetrahedron: Asymmetry 2006, 17, 508[DOI].
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