Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/98322
Title: Direct asymmetric allylic alkenylation of N-itaconimides with Morita–Baylis–Hillman carbonates
Authors: Yang, Wenguo
Tan, Davin
Li, Lixin
Han, Zhiqiang
Yan, Lin
Huang, Kuo-Wei
Tan, Choon-Hong
Jiang, Zhiyong
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
http://hdl.handle.net/10220/17040
DOI: 10.1021/jo3012539
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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