Asymmetric Copper(II)-Catalysed Nitroaldol (Henry) Reactions Utilizing a Chiral C-1-Symmetric Dinitrogen Ligand

作者：Zhou Yirong; Gong Yuefa^*

来源：European Journal of Organic Chemistry, 2011, (30): 6092-6099.

DOI：10.1002/ejoc.201100857

• Asymmetric catalysis
• Chiral dinitrogen ligand
• Copper
• Nitroaldol reaction
• Nucleophilic addition

A series of stable chiral C-1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensation of chiral amines [(-)-exo-bornylamine or (+)-(1S,2S,5R)-menthylamine] with various substituted imidazolecarbaldehydes. With the assistance of base, the ligand L1 in combination with CuCl2.2H2O (2.5 mol-% or 5.0 mol-%) can efficiently promote nitroaldol (Henry) reactions between a variety of aldehydes and nitromethane. Both aromatic and aliphatic aldehydes were tolerated in our catalytic system, affording the expected nitroalcohol products in high yields (up to 97%) and with good enantioselectivities (up to 96%) under mild reaction conditions.

• 出版日期2011-10
• 单位华中科技大学