Highly diastereo- and enantioselective direct aldol reactions by 4-tert-butyldimethylsiloxy-substituted organocatalysts derived from N-prolylsulfonamides in water |
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| Authors: | Shao-dong Fu Xiang-kai Fu Shu-peng Zhang Xiao-chuan Zou Xiao-ju Wu |
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| Institution: | 1. College of Chemistry and Chemical Engineering, Research Institute of Applied Chemistry Southwest University, The Key Laboratory of Applied Chemistry of Chongqing Municipality, Key Laboratory of Eco-environments in Three Gorges Reservoir Region (Ministry of Education), Chongqing 400715, People’s Republic of China;2. School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210091, China |
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| Abstract: | A new set of 4-tert-butyldimethylsiloxy-substituted organocatalysts derived from N-prolylsulfonamide has been designed and proved to be effective in catalyzing the direct aldol reactions of cyclic ketones with a series of aromatic aldehydes. Furthermore, to the best of our knowledge, there are no reports on the aldol reaction generating the products in very good yields (>99%) and with excellent diastereoselectivities up to >99:1 and enantioselectivities up to >99% by using lower catalyst loadings (only 3 mol %), without using any additives in a large amount of water under mild conditions. |
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