Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2012-07-26
Print Publication Date2012-08-03
Permanent link to this recordhttp://hdl.handle.net/10754/562269
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AbstractThe asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity. © 2012 American Chemical Society.
CitationYang, W., Tan, D., Li, L., Han, Z., Yan, L., Huang, K.-W., … Jiang, Z. (2012). Direct Asymmetric Allylic Alkenylation of N-Itaconimides with Morita–Baylis–Hillman Carbonates. The Journal of Organic Chemistry, 77(15), 6600–6607. doi:10.1021/jo3012539
SponsorsFinancial support from the National Natural Science Foundation of China (21072044), Excellent Youth Foundation of Henan Scientific Committee (114100510003), and the Program for New Century Excellent Talents in University of Ministry of Education (NCET-11-0938) is greatly appreciated. We also thank Professor Hongwei Zhou (Zhejiang University) and Professor Fuwei Li (Lanzhou Institute of Chemical Physics) for their generous help in high resolution mass spectrum analysis.
PublisherAmerican Chemical Society (ACS)
JournalThe Journal of Organic Chemistry
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