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Molecules 2015, 20(4), 6224-6236; doi:10.3390/molecules20046224

Cu (II)-Catalyzed Asymmetric Henry Reaction with a Novel C1-Symmetric Aminopinane-Derived Ligand

1
Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432 Ås, Norway
2
Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, P.O. Box 1068, Blindern, N-0316 Oslo, Norway
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 19 February 2015 / Revised: 30 March 2015 / Accepted: 3 April 2015 / Published: 9 April 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [757 KB, uploaded 9 April 2015]   |  

Abstract

A novel C1-symmetric dinitrogen ligand was synthesized in high yield from commercially available (1R,2R,3R,5S)-(−)-isopinocampheylamine and 1-methyl-2-imidazolecarboxaldehyde. In combination with Cu(OAc)2H2O, this new ligand promote the reaction between nitromethane and aliphatic aldehydes with high yields (up to 97%) and moderate enantioselectivities (up to 67% ee). The reactions with benzaldehyde required prolonged reaction time that resulted in diminished yields, but accompanied with ee-values in the 55%–76% range. View Full-Text
Keywords: asymmetric catalysis; Henry reaction; nitrooaldol; chiral ligand; copper asymmetric catalysis; Henry reaction; nitrooaldol; chiral ligand; copper
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Filippova, L.; Stenstrøm, Y.; Hansen, T.V. Cu (II)-Catalyzed Asymmetric Henry Reaction with a Novel C1-Symmetric Aminopinane-Derived Ligand. Molecules 2015, 20, 6224-6236.

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