4.4 Article

Microwave-enhanced bismuth triflate-catalyzed epoxide opening with aliphatic amines

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 9, Pages 1546-1550

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.12.100

Keywords

bismuth; bismuth(III) triflate; epoxide; aliphatic amine; 2-amino alcohol

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In the presence of a catalytic amount of Bi(OTf)(3)-4H(2)O and under microwave irradiation, neat mixtures of epoxides and amines afforded smoothly the corresponding 2-amino alcohols. A wide variety of aliphatic amines were reacted with cycloalkene oxide, styrene oxide, and stilbene oxide. The reaction proceeded rapidly and afforded the 2-amino alcohols in high up to quantitative yields. All products could be obtained without aqueous work-up by simple filtration. (c) 2007 Published by Elsevier Ltd.

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