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Asymmetric Copper(II)‐Catalysed Nitroaldol (Henry) Reactions Utilizing a Chiral C 1 ‐Symmetric Dinitrogen Ligand
Author(s) -
Zhou Yirong,
Gong Yuefa
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100857
Subject(s) - nitromethane , nitroaldol reaction , chemistry , ligand (biochemistry) , catalysis , copper , enantioselective synthesis , medicinal chemistry , condensation , chiral ligand , organic chemistry , combinatorial chemistry , biochemistry , receptor , thermodynamics , physics
A series of stable chiral C 1 ‐symmetric dinitrogen ligands were conveniently synthesized in high yields by condensation of chiral amines [(–)‐ exo ‐bornylamine or (+)‐(1 S ,2 S ,5 R )‐menthylamine] with various substituted imidazolecarbaldehydes. With the assistance of base, the ligand L1 in combination with CuCl 2 · 2H 2 O (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.