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. © 2012 American Chemical Society.
Original language | English (US) |
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Pages (from-to) | 6600-6607 |
Number of pages | 8 |
Journal | The Journal of Organic Chemistry |
Volume | 77 |
Issue number | 15 |
DOIs | |
State | Published - Jul 26 2012 |
ASJC Scopus subject areas
- Organic Chemistry
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CCDC 874217: Experimental Crystal Structure Determination : Methyl 3-(4-bromophenyl)-5-((1-(4-bromophenyl)-4-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)(phenyl)methyl)-4,5-dihydro-1,2-oxazole-5-carboxylate
Yang, W. (Creator), Tan, D. (Creator), Li, L. (Creator), Han, Z. (Creator), Yan, L. (Creator), Huang, K. (Creator), Tan, C. (Creator), Jiang, Z. (Creator), Yang, W. (Creator), Li, L. (Creator), Han, Z. (Creator), Yan, L. (Creator), Tan, C. (Creator), Jiang, Z. (Creator), Yang, W. (Creator), Li, L. (Creator), Han, Z. (Creator), Yan, L. (Creator), Tan, C. (Creator) & Jiang, Z. (Creator), Cambridge Crystallographic Data Centre, 2013
DOI: 10.5517/ccybpkh, http://hdl.handle.net/10754/624688
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