期刊
TETRAHEDRON
卷 61, 期 37, 页码 8939-8946出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.07.008
关键词
asymmetry; diamines; organolithium; imines; catalysis
Enantioselective addition of methyllithium to aromatic imines catalyzed by C-2 symmetric tertiary diamines is described. Eleven diamines have been tested, for which dramatic effect of the nitrogen substitution has been observed. Diamines bearing hindered group close to the nitrogen led to racemic product while homologous hindered diamines led to the best results. Enantiomeric excess up to 74% could be achieved. An explanation of the absolute configuration of the product obtained is given considering the mechanism of the reaction. (c) 2005 Elsevier Ltd. All rights reserved.
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