Download PDF
Synfacts 2007(5): 0546-0546  
DOI: 10.1055/s-2007-968403
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric syn-Selective Direct Aldol Reaction of Linear Aliphatic Ketones

Contributor(s): Benjamin List, Subhas Chandra Pan
S. Luo*, H. Xu, J. Li, L. Zhang, J.-P. Cheng
Chinese Academy of Sciences, Beijing and Nankai University, Tianjin, P. R. of China
Further Information

Publication History

Publication Date:
24 April 2007 (online)

    Permissions and Reprints

Significance

Here the authors report the bifunctional primary-tertiary amine catalyst 1 for a syn-selective direct aldol reaction of linear aliphatic ketones with aromatic aldehydes. Catalyst 1 in combination with TfOH and 3-NO2C6H4COOH has been found to be efficient for this reaction. With ­10 mol% of catalyst 1 good to high diastereoselectivities (dr = 5:1 to 12:1) and high enantioselectivities (er = 92:8 to 99.5:0.5) are obtained for different linear aliphatic ketones. This report shows an effective utilization of a primary-tertiary amine catalyst for enantioselective transformations.