Issue 8, 2016

Enantioselective synthesis of 4H-pyranonaphthoquinones via sequential squaramide and silver catalysis

Abstract

An enantioselective one-pot Michael addition/hydroalkoxylation reaction between 2-hydroxy-1,4-naphthoquinones and alkyne-tethered nitroalkenes catalyzed by a cinchona-derived squaramide and a silver(I) salt has been developed. The sequential protocol provides a direct access to 4H-pyranonaphthoquinones in moderate to very good yields and good to excellent enantioselectivities at a very low catalyst loading (0.5 mol%) of the squaramide.

Graphical abstract: Enantioselective synthesis of 4H-pyranonaphthoquinones via sequential squaramide and silver catalysis

Supplementary files

Article information

Article type
Communication
Submitted
19 Nov 2015
Accepted
02 Dec 2015
First published
03 Dec 2015

Chem. Commun., 2016,52, 1669-1672

Author version available

Enantioselective synthesis of 4H-pyranonaphthoquinones via sequential squaramide and silver catalysis

U. Kaya, P. Chauhan, D. Hack, K. Deckers, R. Puttreddy, K. Rissanen and D. Enders, Chem. Commun., 2016, 52, 1669 DOI: 10.1039/C5CC09592A

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