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Issue 41, 2014
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9-Amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts

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Abstract

A new class of 9-amino-(9-deoxy)cinchona alkaloid-derived chiral phase-transfer catalysts bearing amino groups was developed by using known cinchona alkaloids as the starting materials. Due to the transformation of the 9-hydroxyl group into a 9-amino functional group, the catalytic performances were significantly improved in comparison with the corresponding first generation phase-transfer catalysts, and excellent yields (92–99%) and high enantioselectivities (87–96% ee) were achieved in the benchmark asymmetric α-alkylation of glycine Schiff base. Based on the special contribution of the amino group to the high yield and enantioselectivity, the possible catalytic mechanism was conjectured.

Graphical abstract: 9-Amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts

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Publication details

The article was received on 03 Aug 2014, accepted on 18 Aug 2014 and first published on 19 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB01648C
Citation: Org. Biomol. Chem., 2014,12, 8336-8345
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    9-Amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts

    W. Peng, J. Wan, B. Xie and X. Ma, Org. Biomol. Chem., 2014, 12, 8336
    DOI: 10.1039/C4OB01648C

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