Chakraborti, Asit K. ; Kondaskar, Atul (2003) ZrCl4 as a new and efficient catalyst for the opening of epoxide rings by amines Tetrahedron Letters, 44 (45). pp. 8315-8319. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2003.09.046
Abstract
Zirconium(IV) chloride catalyses the nucleophilic opening of epoxide rings by amines leading to the efficient synthesis of β-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.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
Keywords: | Zirconium; Epoxide; Amine; Regioselectivity |
ID Code: | 100664 |
Deposited On: | 19 Jan 2017 10:16 |
Last Modified: | 19 Jan 2017 10:16 |
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