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|Title:||Direct asymmetric allylic alkenylation of N-itaconimides with Morita–Baylis–Hillman carbonates||Authors:||Yang, Wenguo
|Issue Date:||2012||Source:||Yang, W., Tan, D., Li, L., Han, Z., Yan, L., Huang, K.-W., et al. (2012). Direct Asymmetric Allylic Alkenylation of N -Itaconimides with Morita–Baylis–Hillman Carbonates . The Journal of Organic Chemistry, 77(15), 6600-6607.||Series/Report no.:||The journal of organic chemistry||Abstract:||The 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.||URI:||https://hdl.handle.net/10356/98322
|DOI:||10.1021/jo3012539||Fulltext Permission:||none||Fulltext Availability:||No Fulltext|
|Appears in Collections:||SPMS Journal Articles|
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