A New Strategy for Enantioselective Construction of Multisubstituted Five‐Membered Oxygen Heterocycles via a Domino Michael/Hemiketalization Reaction. Issue 34 (14th July 2015)

• Record Type: Journal Article
• Authors: Hua, Yuan‐Zhao; Liu, Meng‐Meng; Huang, Pei‐Jin; Song, Xixi; Wang, Min‐Can; Chang, Jun‐Biao
• Is Part Of: Chemistry. Volume 21:Issue 34(2015)
• Page Start: 11994
• Page End: 11998
• Publication Date: 2015-07-14
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201501655
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 ZnEt₂, the corresponding <italic>anti</italic>‐multisubstituted tetrahydrofuran products were obtained in up to 90 % yields, and 98 % enantiomeric excess (<italic>ee</italic>) 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.</p> </abstract>