Journal
TETRAHEDRON-ASYMMETRY
Volume 24, Issue 7, Pages 380-388Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2013.02.013
Keywords
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Funding
- Natural Science Foundation of China [Y4080450]
- Shaoxing University [20115025]
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An efficient, solvent-free protocol for the asymmetric aldol reaction between aldehydes and ketones using prolinamides 1-4 as organocatalysts is reported. Catalysts 2-4, in the presence of TFA (the ratio of catalyst and TFA = 1/1.5), proved to be excellent catalysts, giving the aldol products between aromatic aldehydes and ketones with nearly perfect diastereo- and enantioselectivities (up to >99:1 dr and >99% ee). This catalytic system can also be applied in the cross-aldol reaction of isatin with ketones and the Michael reaction between cyclohexane and nitroalkenes. A mechanism is proposed to account for the formation of the major enantiomer in this reaction. (c) 2013 Elsevier Ltd. All rights reserved.
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