Issue 72, 2021

Generation of zwitterionic trifluoromethyl N-allylic ylides and their use in switchable divergent annulations

Abstract

The previously unreported zwitterionic N-allylic ylide species from the corresponding Morita–Baylis–Hillman carbonates of trifluoromethyl ketones and acrylonitrile are generated under the catalysis of cinchona-derived tertiary amines, and subsequently participate in switchable asymmetric [3+2] or [4+1] annulations with 1-azadienes in chemo-, regio-, and stereodivergent manners via catalyst or substrate control. A diverse range of frameworks, having a trifluoromethylated all-carbon quaternary stereogenic centre or a tetrasubstituted alkene moiety, are generally constructed in good yields with excellent enantioselectivity.

Graphical abstract: Generation of zwitterionic trifluoromethyl N-allylic ylides and their use in switchable divergent annulations

Supplementary files

Article information

Article type
Communication
Submitted
15 Jul 2021
Accepted
09 Aug 2021
First published
09 Aug 2021

Chem. Commun., 2021,57, 9056-9059

Generation of zwitterionic trifluoromethyl N-allylic ylides and their use in switchable divergent annulations

R. Yan, B. Liu, Y. Hu, W. Du and Y. Chen, Chem. Commun., 2021, 57, 9056 DOI: 10.1039/D1CC03830C

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