Abstract
Two novel amphiphilic l-proline derivatives bearing long alkyl chain on the 4-position via ether bonds, 1a and 1b, have been synthesized and evaluated for the asymmetric direct aldol reaction in organic solvents as well as in water. The catalytic activities with 5 mol% of 1a are better than that of 30 mol% of proline itself being used. Especially, high yields (up to 99%), excellent enantioselectivities (up to 99% ee) and anti-diastereoselectivities (up to 99:1) are achieved in the reactions of aromatic aldehydes and cyclic ketones at room temperature with 5 mol% of 1a in water.
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Acknowledgments
We are grateful for the financial support from the Natural Science Foundation of China (No. 20372059, 20772113). We also thank Yu Zhu for the determination of single crystal structure, Jian-Xun Kang and Wei-Guo Zhu for the NMR, Shao-Min Wang for HRMS.
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Fu, YQ., An, YJ., Liu, WM. et al. Highly Diastereo- and Enantioselective Direct Aldol Reaction Catalyzed by Simple Amphiphilic Proline Derivatives. Catal Lett 124, 397–404 (2008). https://doi.org/10.1007/s10562-008-9492-7
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DOI: https://doi.org/10.1007/s10562-008-9492-7