A C1-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones. Issue 28 (24th April 2018)

• Record Type: Journal Article
• Authors: Lin, Jun-Bing; Cheng, Xi-Na; Tian, Xiao-Dong; Xu, Guo-Qiang; Luo, Yong-Chun; Xu, Peng-Fei
• Is Part Of: RSC advances. Volume 8:Issue 28(2018)
• Page Start: 15444
• Page End: 15447
• Publication Date: 2018-04-24
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8ra02009d
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A NHC-catalysed spiroannulation of isatin-derived enals and 1, 3-dicarbonyl compounds has been developed, enabling enantioselective synthesis of synthetically important spirooxindole δ-lactones. Abstract : A C1 -symmetric N -heterocyclic carbene (NHC)-catalysed activation of isatin-derived enals under oxidative conditions was achieved. The in situ generated α, β-unsaturated acyl azolium species was efficiently trapped by 1, 3-dicarbonyl compounds via a Michael addition/spiroannualtion cascade, delivering a series of synthetically important spirooxindole δ-lactones with up to 96% enantioselectivity.