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

Wenguo Yang, Davin Tan, Lixin Li, Zhiqiang Han, Lin Yan, Kuo-Wei Huang, Choonhong Tan, Zhiyong Jiang

Research output: Contribution to journalArticlepeer-review

26 Scopus citations


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. © 2012 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)6600-6607
Number of pages8
JournalThe Journal of Organic Chemistry
Issue number15
StatePublished - Jul 26 2012

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Financial 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.

ASJC Scopus subject areas

  • Organic Chemistry


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