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Synthesis 2009(20): 3433-3438
DOI: 10.1055/s-0029-1216956
DOI: 10.1055/s-0029-1216956
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Erbium(III) Triflate is a Highly Efficient Catalyst for the Synthesis of β-Alkoxy Alcohols, 1,2-Diols and β-Hydroxy Sulfides by Ring Opening of Epoxides
Weitere Informationen
Received
25 May 2009
Publikationsdatum:
21. August 2009 (online)
Publikationsverlauf
Publikationsdatum:
21. August 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200920/lookinside/thumbnails/10.1055-s-0029-1216956-1.jpg)
Abstract
Chemo- and stereoselectivity in the ring-opening reaction of epoxides with erbium(III) triflate are described. Epoxides can be cleaved under neutral conditions with alcohols and thiols in the presence of catalytic amounts of Lewis acid, affording the corresponding β-alkoxy alcohols and β-hydroxy sulfides in high yields. In water, epoxide ring opening occurs to produce the corresponding diols in good yields
Key words
epoxides - Lewis acids - nucleophilic additions - ring opening - green chemistry
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References
A 0.1 M aqueous solution of Er(OTf)3 is only weakly acidic (pH ca. 5.9), and the aqueous layer from workup is even less acidic (pH ca. 6.6).