d-Mannitol-derived novel chiral thioureas: Synthesis and application in asymmetric Henry reactions |
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Authors: | Miaoxi Liu Nan Ji Li Wang Peng Liu Wei He |
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Institution: | 1. Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi''an 710032, PR China;2. School of Pharmacy, Xi''an Medical University, Xi''an 710021, PR China |
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Abstract: | Five novel thioureas have been obtained through multi-step reactions from d-Mannitol as starting material and applied as catalysts in the asymmetric Henry reaction. Using catalyst 7a, (1S,2R)-2-nitro-1-phenylpropan-1-ol containing two chiral centers was obtained in high yield and with high selectivity (up to 95% yield, 87% ee, 91:9 dr). This catalyst also retained activity in the presence of water, affording a up to 93% yield, 88% ee, and 94:6 dr. |
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Keywords: | Asymmetric catalysis Oxaziridination Cinchonaalkaloids Organic catalysis |
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