Issue 23, 2020

The dual alkylation of the C(sp3)–H bond of cyclic α-methyl-N-sulfonyl imines via the sequential condensation/hydride transfer/cyclization process

Abstract

The dual alkylation of the C(sp3)–H bond of cyclic α-methyl-N-sulfonyl imines has been achieved through the piperidine-promoted cascade condensation/[1,5]-hydride transfer/cyclization sequence from cyclic α-methyl-N-sulfonyl imines and o-aminobenzaldehydes in trifluoroethanol, providing structurally diverse 3-cyclic N-sulfonyl imine substituted tetrahydroquinolines in good yields with excellent diastereoselectivities.

Graphical abstract: The dual alkylation of the C(sp3)–H bond of cyclic α-methyl-N-sulfonyl imines via the sequential condensation/hydride transfer/cyclization process

Supplementary files

Article information

Article type
Research Article
Submitted
12 Aug 2020
Accepted
17 Oct 2020
First published
19 Oct 2020

Org. Chem. Front., 2020,7, 3868-3873

The dual alkylation of the C(sp3)–H bond of cyclic α-methyl-N-sulfonyl imines via the sequential condensation/hydride transfer/cyclization process

K. Yuan, F. Dong, X. Yin, S. Li, L. Wang and L. Xu, Org. Chem. Front., 2020, 7, 3868 DOI: 10.1039/D0QO00972E

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