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

Molecules

Liudmila Filippova¹  Yngve Stenstrøm¹  Trond Vidar Hansen¹ 

[1] Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432 Ås, Norway; E-Mail:

关键词: asymmetric catalysis;    Henry reaction;    nitrooaldol;    chiral ligand;    copper;   

DOI  :  10.3390/molecules20046224

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.