- Selective C-H bond hydroxylation of cyclohexanes in water by supramolecular control
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A new approach for selective hydroxylation of non-activated cyclohexanes using dioxirane generated in situ in water through supramolecular control has been developed. Using β-CD and γ-CD as the supramolecular hosts, selective hydroxylation of cyclohexane substrates, including trans/cis-1,4-, 1,3-and 1,2-dimethylcyclohexanes and trans/cis-decahydronaphthalene, was achieved in up to 54% yield in water. Furthermore, site-selective C-H bond hydroxylation of (+)-menthol was achieved by obstructing the approach of dioxirane to the C-H bond with higher steric hindrance through inclusion complexation with β-CD and γ-CD in water.
- Yang, Bin,Cui, Jian-Fang,Wong, Man Kin
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- Cyclohexane-based 1,3-Dipodands; Complexation and Conformational Biasing
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Cyclohexane-based cis-1,3-dipodand (1) undergoes ring inversion to a diaxial conformation upon Na(1+) complexation, while related diaxially biased dipodand (2) is a better host.
- Shirodkar, Shailaja M.,Weisman, Gary R.
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