Issue 19, 2019

Asymmetric domino 1,6-addition/annulation reaction of 3-cyano-4-alkenyl-2H-chromen-2-ones with isatin-derived MBH carbonates: enantioselective synthesis of 3,3′-cyclopentenylspirooxindoles bearing 2H-chromen-2-ones

Abstract

An asymmetric domino 1,6-addition/annulation reaction of 3-cyano-4-alkenyl-2H-chromen-2-ones with isatin-derived MBH carbonates was achieved. With this developed protocol, a series of 3,3′-cyclopentenylspirooxindoles bearing 2H-chromen-2-ones were obtained in moderate to excellent yields with good to excellent diastereo- and enantioselectivities (>20 : 1 dr, up to 97 : 3 er).

Graphical abstract: Asymmetric domino 1,6-addition/annulation reaction of 3-cyano-4-alkenyl-2H-chromen-2-ones with isatin-derived MBH carbonates: enantioselective synthesis of 3,3′-cyclopentenylspirooxindoles bearing 2H-chromen-2-ones

Supplementary files

Article information

Article type
Research Article
Submitted
14 jul 2019
Accepted
12 aug 2019
First published
14 aug 2019

Org. Chem. Front., 2019,6, 3342-3347

Asymmetric domino 1,6-addition/annulation reaction of 3-cyano-4-alkenyl-2H-chromen-2-ones with isatin-derived MBH carbonates: enantioselective synthesis of 3,3′-cyclopentenylspirooxindoles bearing 2H-chromen-2-ones

Z. Wang, C. Lei, X. Zhang, Y. You, J. Zhao and W. Yuan, Org. Chem. Front., 2019, 6, 3342 DOI: 10.1039/C9QO00890J

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