Direct Asymmetric Allylic Alkenylation of N-Itaconimides with Morita–Baylis–Hillman Carbonates
The Journal of Organic Chemistry2012Vol. 77(15), pp. 6600–6607
Citations Over TimeTop 18% of 2012 papers
Wenguo Yang, Davin Tan, Lixin Li, Zhiqiang Han, Lin Yan, Kuo‐Wei Huang, Choon‐Hong Tan, Zhiyong Jiang
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.
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