Cu (II)-catalyzed asymmetric henry reaction with a novel C1-symmetric aminopinane-derived ligand

Liudmila Filippova; Yngve Stenstrøm; Trond Vidar Hansen

doi:10.3390/molecules20046224

Cu (II)-catalyzed asymmetric henry reaction with a novel C1-symmetric aminopinane-derived ligand

Molecules. 2015 Apr 9;20(4):6224-36. doi: 10.3390/molecules20046224.

Authors

Liudmila Filippova¹, Yngve Stenstrøm², Trond Vidar Hansen^{3

4}

Affiliations

¹ Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432 Ås, Norway. liudmila.filippova@nmbu.no.
² Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432 Ås, Norway. yngve.stenstrom@nmbu.no.
³ Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432 Ås, Norway. t.v.hansen@farmasi.uio.no.
⁴ Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, P.O. Box 1068, Blindern, N-0316 Oslo, Norway. t.v.hansen@farmasi.uio.no.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzaldehydes / chemistry
Bicyclic Monoterpenes
Catalysis*
Copper / chemistry*
Ligands
Methane / analogs & derivatives
Methane / chemistry
Molecular Structure
Nitroparaffins / chemistry
Stereoisomerism
Terpenes / chemical synthesis
Terpenes / chemistry*

Substances

Benzaldehydes
Bicyclic Monoterpenes
Ligands
Nitroparaffins
Terpenes
pinane
Copper
Methane
nitromethane
benzaldehyde