Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, P.R. China
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State Key Laboratory of Chiroscience and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong
Chem. Commun., 2013,49, 6713-6715
27 Feb 2013,
15 Apr 2013
First published online
16 Apr 2013
A new chiral bis-phosphoric acid 3l bearing triple axial chirality was synthesized and applied to effect a highly enantioselective 1,3-dipolar cycloaddition reaction between N,N′-azomethine imines and methyleneindolinones for the creation of chiral spiro[pyrazolidin-3,3′-oxindoles] in excellent yields and selectivities. MS experiment and DFT calculation studies prompted us to propose a dual H-bond donor activation mode of bis-phosphoric acid which is different from the traditional phosphoric acid catalysis.
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