Liming Zhang
Assistant Professor
Organic and Bioorganic Chemistry
B.S. (1993), Nanchang University; M.S. (1996), Nankai University; M.S. (1998), University of Alabama; Ph.D. (2003), University of Michigan (Masato Koreeda); Postdoctoral (2003-2005), University of Chicago (Sergey A. Kozmin).
E-mail: lzhang![[at]](../images/at.png)
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Liming Zhang
Research Interests
We are interested in both development of novel chemical transformations, especially those of transition-metal catalysis, and total synthesis of natural products with significant biological activities.
Au-Catalyzed Tandem Reactions
Au salts have been shown as exceptional catalysts to activate alkynes for nucleophilic reactions. However, Au-catalyzed activation of allenes has not been studied much. We are interested in general in Au-catalyzed reactions of allenes. Currently we are studying the reactivities of allenyl esters in the presence of gold catalysts. Those allenyl esters can be generated in situ from readily available propargylic esters via the catalysis of the very same Au salts. A range of efficient Au-catalyzed tandem reactions of propargylic esters leading to novel structures and synthetically important intermediates have been developed. Examples are shown below.
Phosphoranyl Radical-Mediated Deoxygenative Reactions
Phosphoranyl radicals can induce deoxygenation through chemo- and regio-selective fragmentation of more hindered C-O bonds. Our efforts will be focused on developing new methods for deoxygenation of carbonyl compounds mediated by phosphoranyl radicals under neutral and mild radical reaction conditions.
Natural Products Synthesis
We are also interested in the total synthesis of Pelorusida A and Variecolin. Peloruside A is microtubule-stabilizing agent and Variecolin is a potent immunosuppressant. Successful synthesis of these biologically important compounds will provide ready access to their structural analogs, facilitating their SAR studies.
Selected Publications
“PtCl2-catalyzed rapid access to tetracyclic 2,3-indoline-fused cyclopentenes: Reactivity divergent from cationic Au(I) catalysis and synthetic potential,” Zhang, G.; Catalano, V.J.; Zhang, L. J. Am. Chem. Soc. 2007, accepted.
“Gold-catalyzed intramolecular redox reaction of sulfinyl alkynes: Efficient generation of a-oxo gold carbenoids and application in insertion into R-CO bonds,” Li, G.; Zhang, L. Angew. Chem. Int. Ed. 2007, 46, 5156-5159.
“Two-step formal [3+2] cycloaddition of enones/enals and allenyl MOM ether: Gold-catalyzed highly diastereoselective synthesis of cyclopentanone enol ether containing an all-carbon quaternary center,” Huang, X.; Zhang, L. J. Am. Chem. Soc. 2007, 129, 6398-6399.
“A gold-catalyzed unique cycloisomerization of 1,5-enynes: Efficient formation of 1-carboxycyclohexa-1,4-dienes and carboxyarenes,” Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 14274-14275.
“Efficient synthesis of cyclopentenones from enynyl acetates via tandem Au(I)-catalyzed 3,3-rearrangement and the Nazarov reaction,” Zhang, L.; Wang, S. J. Am. Chem. Soc. 2006, 128, 1442-1443.
“Tandem Au-catalyzed 3,3-rearrangement-[2 + 2] cycloadditions of propargylic esters: Expeditious access to highly functionalized 2,3-indoline-fused cyclobutanes,” Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804-16805.