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Synlett 2001; 2001(6): 0836-0838
DOI: 10.1055/s-2001-14909
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Ytterbium Trifluoromethanesulfonate Yb(OTf)3: An Efficient, Reusable Catalyst for Highly Selective Formation of β-Alkoxy Alcohols via Ring-Opening of 1,2-Epoxides with Alcohols

Pravin R. Likhar* , Manyam Praveen Kumar, Ananda K. Bandyopadhyay
  • *Metalorganic Laboratory, Inorganic Chemistry Division, Indian Institute of Chemical Technology, Hyderbad 500 007, India; Fax + 91-40-717-0921; E-mail: akbandyopadyay@iict.ap.nic.in
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Publication Date:
31 December 2001 (online)

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Ytterbium(III)triflate-catalysed ring-opening reactions of epoxides derived from styrene, cyclohexene, norbornene and stilbene, in the presence of alcohols (C1-C4 1°, 2° and 3° aliphatic alcohols, cyclohexyl alcohol, allyl and propargyl alcohol) resulted in the formation of β-alkoxy alcohols in good to excellent yield with high regio-, and where applicable, stereoselectivity. Reaction of stilbene oxide with methanol in the presence of the diethyl ester of l-(+)-tartaric acid afforded the threo form of 1,2-diphenyl-2-methoxy ethanol with high diastereoselectivity (de 94%). Mechanistic implications of the results are discussed.

ytterbium triflate catalyst - ring-opening of epoxide - β-alkoxy alcohol - diastereoselective reaction - eco-friendly process