Direct asymmetric allylic alkenylation of N-itaconimides with Morita–Baylis–Hillman carbonates

Direct asymmetric allylic alkenylation of N-itaconimides with Morita–Baylis–Hillman carbonates

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 yi...

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Bibliographic Details
Main Authors: Yang, Wenguo, Tan, Davin, Li, Lixin, Han, Zhiqiang, Yan, Lin, Huang, Kuo-Wei, Tan, Choon-Hong, Jiang, Zhiyong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2013
Online Access:https://hdl.handle.net/10356/98322
http://hdl.handle.net/10220/17040
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Institution: Nanyang Technological University
Language: English
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Summary: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.

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