Issue 2, 2017

Cobalt(ii)/(imidazoline–oxazoline)-catalyzed enantioselective Michael addition of 2-acetyl azaarenes to β-CF3-β-disubstituted nitroalkenes

Abstract

A series of chiral (imidazoline–oxazoline) N,N-bidentate ligands L1–L5 derived from 2,2-dimethylmalonic acid were conveniently synthesized and characterized. With the aid of the new ligands, the first Co(II)-catalyzed asymmetric Michael addition of 2-acetyl azaarenes to β-CF3-β-disubstituted nitroalkenes was successfully achieved, producing chiral compounds with a trifluoromethylated all-carbon quaternary stereocenter in good yields with enantioselectivities of up to 98% ee.

Graphical abstract: Cobalt(ii)/(imidazoline–oxazoline)-catalyzed enantioselective Michael addition of 2-acetyl azaarenes to β-CF3-β-disubstituted nitroalkenes

Supplementary files

Article information

Article type
Research Article
Submitted
19 Sep 2016
Accepted
24 Nov 2016
First published
25 Nov 2016

Org. Chem. Front., 2017,4, 308-312

Cobalt(II)/(imidazoline–oxazoline)-catalyzed enantioselective Michael addition of 2-acetyl azaarenes to β-CF3-β-disubstituted nitroalkenes

X. Hao, C. Wang, S. Liu, X. Wang, L. Wang, J. Gong and M. Song, Org. Chem. Front., 2017, 4, 308 DOI: 10.1039/C6QO00562D

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