Issue 43, 2017

Enantioselective alkynylation of N-sulfonyl α-ketiminoesters via a Friedel–Crafts alkylation strategy

Abstract

Enantioselective alkynylation of cyclic N-sulfonyl α-ketiminoesters with terminal alkynes was developed by using an Ni(ClO4)2/(R)-DTBM-Segphos complex as a catalyst. A range of propargylic amides bearing quaternary stereocenters were afforded in excellent enantioselectivities (up to 97% ee). Theoretical studies revealed that this reaction proceeded via a Friedel–Crafts-type reaction pathway.

Graphical abstract: Enantioselective alkynylation of N-sulfonyl α-ketiminoesters via a Friedel–Crafts alkylation strategy

Supplementary files

Article information

Article type
Communication
Submitted
08 Feb 2017
Accepted
10 May 2017
First published
10 May 2017

Chem. Commun., 2017,53, 5890-5893

Enantioselective alkynylation of N-sulfonyl α-ketiminoesters via a Friedel–Crafts alkylation strategy

R. Liu, L. Zhu, J. Hu, C. Lu, J. Gao, Y. Lan and Y. Jia, Chem. Commun., 2017, 53, 5890 DOI: 10.1039/C7CC01015J

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