title: Direct asymmetric allylic alkenylation of N-itaconimides with Morita-Baylis-Hillman carbonates.
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.
authors: Institute of Chemical Biology, Henan University, Kaifeng, Henan, P. R. China, 475004.
authors: Wenguo
authors: W
authors: Yang
authors: Davin
authors: D
authors: Tan
authors: Lixin
authors: L
authors: Li
authors: Zhiqiang
authors: Z
authors: Han
authors: Lin
authors: L
authors: Yan
authors: Kuo-Wei
authors: KW
authors: Huang
authors: Choon-Hong
authors: CH
authors: Tan
authors: Zhiyong
authors: Z
authors: Jiang
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry*; D002930:Cinchona Alkaloids / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000498:Allyl Compounds; D002254:Carbonates; D002930:Cinchona Alkaloids