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A New Strategy for Enantioselective Construction of Multisubstituted Five‐Membered Oxygen Heterocycles via a Domino Michael/Hemiketalization Reaction
Author(s) -
Hua YuanZhao,
Liu MengMeng,
Huang PeiJin,
Song Xixi,
Wang MinCan,
Chang JunBiao
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501655
Subject(s) - enantioselective synthesis , domino , chemistry , tetrahydrofuran , intramolecular force , cascade reaction , michael reaction , denticity , enantiomeric excess , zinc , ligand (biochemistry) , organic chemistry , medicinal chemistry , enantiomer , catalysis , combinatorial chemistry , receptor , biochemistry , solvent , crystal structure
A new highly enantioselective domino Michael/hemiketalization reaction of α‐hydroxyacetophenone with β,γ‐unsaturated α‐keto esters for the synthesis of 2,2,4,5‐tetrasubstituted chiral tetrahydrofurans is reported. With 2 mol % intramolecular dinuclear zinc‐AzePhenol complex prepared in situ from the reaction of multidentate semi‐azacrown ether ligand with ZnEt 2 , the corresponding anti ‐multisubstituted tetrahydrofuran products were obtained in up to 90 % yields, and 98 % enantiomeric excess ( ee ) at 0 °C for 45 min. Moreover, the products were easily converted to 2,3,5‐trisubstituted 2,3‐dihydrofurans without any loss in optical activity.