title: Asymmetric inverse-electron-demand hetero-Diels-Alder reaction for the construction of bicyclic skeletons with multiple stereocenters by using a bifunctional organocatalytic strategy: an efficient approach to chiral macrolides.
abstract: We have performed the first bifunctional organocatalytic highly enantioselective inverse-electron-demand hetero-Diels-Alder reaction of cyclic ketones with enones to afford densely functionalized bicyclic skeletons that contain three stereocenters (up 82% yield, 10:1 d.r., and 97% ee). Unlike the previous IEDDAR catalytic strategy, this method features a double HOMO(dienophile)/ LUMO(diene)-activated pathway. Moreover, this process provides a promising method for the construction of enantioenriched macrolides.
authors: Key Laboratory of Preclinical Study for New Drugs, Gansu Province, Institute of Biochemistry and Molecular Biology, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, P. R. China.
authors: Xianxing
authors: X
authors: Jiang
authors: Long
authors: L
authors: Wang
authors: Ming
authors: M
authors: Kai
authors: Liping
authors: L
authors: Zhu
authors: Xiaojun
authors: X
authors: Yao
authors: Rui
authors: R
authors: Wang
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D007659:Ketones / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D007659:Ketones; D018942:Macrolides