Synthesis and Lewis acid catalyzed Claisen rearrangement of 2-(1,3-oxazolin-2-yl)-substituted allyl vinyl ethers |
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Authors: | Hannes HelmboldtMartin Hiersemann |
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Affiliation: | Institut für Organische Chemie, Technische Universität Dresden, Bergstraße 66, D-01069 Dresden, Germany |
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Abstract: | Allyl vinyl ethers containing an acceptor function in the 2-position are useful substrates for the Lewis acid-catalyzed Claisen rearrangement. The first synthesis of acyclic 2-(1,3-oxazolin-2-yl)-substituted allyl vinyl ethers is reported. The Lewis acid catalyzed Claisen rearrangement of these allyl vinyl ethers afforded the rearrangement products with low to moderate diastereo- and enantioselectivity. The catalyzed rearrangement of chiral allyl vinyl ethers was investigated. The combination of substrate- and catalyst-induced diastereoselectivity led to unexpected and unprecedented results. |
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Keywords: | Claisen rearrangement catalysis Lewis acid copper(II) bis(oxazoline) allyl vinyl ether |
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