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)2∙H2O, 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.
Several microorganisms produce small quantities of polyunsaturated hydrocarbons and such natural products are of interest. Starting from the ethyl ester of eicosapentaenoic acid, the total synthesis of the natural product (all-Z)-hentriaconta-3,6,9,12,15,19,22,25,28-nonaene has been achieved in eight steps and 15% overall yield. The synthesis is based on a stereoselective Wittig reaction and confirms the all-Z-configuration of the nine double bonds in this highly unsaturated natural product.
An Asymmetric Iodolactonization Reaction Catalyzed by a Zinc Bis-proline--Phenol Complex. -The application of Trost's di-nuclear zinc complex in catalytic asymmetric iodocyclizations of 5-substituted 5-hexenoic acid derivatives using NIS is demonstrated. -(FILIPPOVA, L.; STENSTROEM*, Y.; HANSEN, T. V.; Tetrahedron Lett. 55 (2014) 2, 419-422, http://dx.
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