期刊
TETRAHEDRON LETTERS
卷 53, 期 5, 页码 570-574出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.11.094
关键词
Indium; Henry reaction; Bromonitroalkanes; Ultrasound; NMR
资金
- Spanish Ministry of Science and Innovation [CTQ2008-06493, CTQ2009-08490]
- Spanish Ministry of Science and Innovation for an FPU
A novel method for the preparation of 2-nitroalkan-1 -ols by an indium-promoted reaction of bromonitromethane and 2-bromonitropropane with a variety of aldehydes was recently reported. Extension of the procedure to 1-bromo-1-nitroethane, which gives rise to a new chiral centre, was considered. On the basis of the diastereoselectivity of the nitroalkanols formed and NMR studies on the reaction mixtures, a mechanistic proposal for the indium-promoted reaction of bromonitroalkanes and aldehydes is discussed. The proposed mechanism allows the prediction of the stereochemical outcome of the present reaction. (C) 2011 Elsevier Ltd. All rights reserved.
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