Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 19, Issue 14, Pages 3895-3898Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2009.03.097
Keywords
Henry reaction; Nitroaldol reaction; Guanidine; Organocatalysis; Asymmetric catalysis
Categories
Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [19020006]
- JSPS
- Grants-in-Aid for Scientific Research [19020006] Funding Source: KAKEN
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The enantioselective activation of nitroalkanes was attempted on the basis of the complexation between chiral guanidinium and nitronate through two hydrogen bonds. The proposed enantioselective activation was applied to the diastereo- and enantioselective Henry (nitroaldol) reaction of nitroalkanes with aldehydes using axially chiral guanidine bases as the catalyst. Optically active nitroaldol products were obtained in acceptable yields with fairly good enantio- and diastereoselectivities at low temperature. (C) 2009 Elsevier Ltd. All rights reserved.
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