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Synthesis and Lewis acid catalyzed Claisen rearrangement of 2-(1,3-oxazolin-2-yl)-substituted allyl vinyl ethers

✍ Scribed by Hannes Helmboldt; Martin Hiersemann

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 245 KB
Volume: 59
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)00590-8

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✦ Synopsis

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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