期刊
TETRAHEDRON LETTERS
卷 44, 期 45, 页码 8315-8319出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2003.09.046
关键词
zirconium; epoxide; amine; regioselectivity
Zirconium(IV) chloride catalyses the nucleophilic opening of epoxide rings by amines leading to the efficient synthesis of beta-amino alcohols. The reaction works well with aromatic and aliphatic amines in short times at room temperature in the absence of solvent. Exclusive trans stereoselectivity is observed for cyclic epoxides. Aromatic amines exhibit excellent regioselectivity for preferential nucleophilic attack at the sterically less hindered position during the reaction with unsymmetrical epoxides. However. in case of styrene oxide. selective formation of the benzylic amine was observed during the reactions with aromatic amines. (C) 2003 Elsevier Ltd. All rights reserved.
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