A novel Prins-alkynylation reaction for the synthesis of 4-phenacyl tetrahydropyrans |
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| Authors: | J.S. Yadav B.V. Subba Reddy Y. Jayasudhan Reddy Bh. Phaneendra Reddy P. Adinarayana Reddy |
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| Affiliation: | Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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| Abstract: | Aldehyde, homoallylic alcohol, and alkyne undergo smooth Prins-type cyclization in the presence of BF3·OEt2/CuCl (10 mol % each) in dichloromethane under mild reaction conditions to afford 4-phenacyl tetrahydropyran derivatives in good yields. This method is highly stereoselective, affording cis-tetrahydropyrans exclusively. The salient features of this method are high conversions, mild reaction conditions, short reaction times, high selectivity, and operational simplicity. |
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| Keywords: | Prins-cyclization BF3· OEt2 Alkynylation Copper acetylides 4-Phenyl tetrahydropyrans |
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