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A rare case of facial selectivity inversion for Sharpless asymmetric dihydroxylation in a series of structurally homogeneous substrates: synthesis of non-racemic 3-(nitrophenoxy)-propane-1,2-diols
Institution:1. DISTAV, University of Genoa, Corso Europa 26, I-16132 Genova, Italy;2. Lamont-Doherty Earth Observatory of Columbia University, 61 Rt. 9W, Palisades, NY 10964, USA;3. Dipartimento di Scienze della Terra, University of Milan, via Botticelli 23, 20133 Milano, Italy;4. Max-Planck-Institut für Chemie, Postfach 3060, 55020 Mainz, Germany;5. Department of Earth and Environmental Sciences, Columbia University, 61 Rt. 9W, Palisades, NY 10964, USA
Abstract:Asymmetric dihydroxylation of mono nitrophenyl allyl ethers leads to the corresponding non-racemic 3-(nitrophenoxy)-propane-1,2-diols 1ac. As this takes place, regardless of the reagent used (AD-mix-α or AD-mix-β), the configuration of the predominant enantiomer for the para- and meta-nitrosubstituted products is opposite to the configuration of the ortho-nitrophenyl derivative. A correlation between the melting points and vibrational spectra of the racemic and enantiopure diols 1ac allowed us to establish that all of the chiral substances investigated formed stable racemic compounds in the solid phase.
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