Asymmetric Henry reaction catalyzed by oxazolinyl
Luo Mei Æ Yin Hao Æ Zhang Jia Hai Æ Hu Ke Liang Æ
Pang Wen Min
Received: 14 October 2007 / Accepted: 23 August 2008 / Published online: 21 January 2009
Ó Springer Science+Business Media B.V. 2009
Abstract A novel family of oxazolinyl copper(II) catalysts have been developed
and used as Lewis acid catalysts in the asymmetric Henry reaction of various alde-
hydes with nitromethane. The corresponding nitroalcohol products were obtained in
moderate yields (40–80%) and with moderate enantioselectivity (10–40% ee).
Keywords Oxazolinyl copper(II) catalysts Á Lewis acid catalysts Á
Henry reaction Á Nitroalcohol
The Henry reaction or the nitroaldol reaction is an important organic reaction
involving formation of a C–C bond. The product of the reaction is a b-nitroalcohol
which can be converted to a variety of products for bearing nitro and alcohol
functional groups [1–3].
Much literature has reported the synthetic method, which can be divided into two
categories: metal/chiral ligand complex-based reactions and organocatalytic reac-
tions [4–9]. Progress in this reaction has been reviewed by two groups [10, 11].
However, limited information is available about the excellent ee% at room
temperature and the simple structures of the catalysts. A major question that must be
addressed is how to obtain the products efﬁciently. In this article we report careful
research on the Henry reaction in which we obtained good yields (40–80%) and
moderate enantioselectivity (10–40% ee).
L. Mei (&)
Department of Chemical Engineering, Hefei University of Technology, Hefei 230009, China
Y. Hao Á Z. J. Hai Á H. K. Liang Á P. W. Min
University of Science and Technology of China, Hefei 230009, China
Res Chem Intermed (2009) 35:123–136