Metal- and Acid-Free Methyl Triflate Catalyzed Meyer–Schuster Rearrangement

Abstract A novel metal- and acid-free preparation of synthetically useful α,β-unsaturated carbonyl compounds from propargyl alcohols has been realized. This Meyer–Schuster rearrangement process is effectively catalyzed by methyl triflate (20 mol%) to prepare a broad scope of conjugated E -enals and...

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Published in:Synthesis (Stuttgart) 2017-07, Vol.49 (14), p.3149-3156
Main Authors: Yang, Lu, Zeng, Qingle
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Language:English
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Zeng, Qingle
description Abstract A novel metal- and acid-free preparation of synthetically useful α,β-unsaturated carbonyl compounds from propargyl alcohols has been realized. This Meyer–Schuster rearrangement process is effectively catalyzed by methyl triflate (20 mol%) to prepare a broad scope of conjugated E -enals and E -enones generally in good to excellent yields (up to 90%). This reaction procedure operates under mild conditions (70 °C), in air, with short reaction times (1 h). Moreover, a carbocation intermediate trapped by the solvent 2,2,2-trifluoroethanol was isolated during this transformation.
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title Metal- and Acid-Free Methyl Triflate Catalyzed Meyer–Schuster Rearrangement
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