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Synfacts 2011(3): 0281-0281  
DOI: 10.1055/s-0030-1259469
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of Tertiary Trifluoromethyl Alcohols

Contributor(s): Mark Lautens, Norman Nicolaus
H. Xu, C. Wolf*
Georgetown University, Washington D.C., USA
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Publication History

Publication Date:
16 February 2011 (online)

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Significance

The asymmetric version of the ­nitroaldol reaction (Henry reaction) is a useful transformation to prepare enantiomerically pure β-hydroxy nitroalkanes, which can be easily ­converted into useful building blocks, such as β-amino acids or aziridines. Herein, the authors describe an efficient copper(II)-catalyzed asymmetric nitroaldol reaction of 1,1,1-trifluoroketones and nitromethane using the chiral bisoxazolidine ligand 4.