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N-heterocyclic carbene-catalyzed Ireland-Coates claisen rearrangement: Synthesis of functionalized β-lactones

Journal of the American Chemical Society, ISSN: 0002-7863, Vol: 135, Issue: 1, Page: 58-61
2013
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Article Description

The N-heterocyclic carbene (NHC)-catalyzed Claisen rearrangement of hybrid Ireland-Coates structures has been achieved, allowing the stereoselective synthesis of highly functionalized β-lactones. The reaction proceeds with high diastereoselectivity (>20:1) and affords a diverse range of β-lactone fused cyclopentanes. Mechanistic studies are detailed. © 2012 American Chemical Society.

Bibliographic Details

Candish, Lisa; Lupton, David W

American Chemical Society (ACS)

Chemical Engineering; Chemistry; Biochemistry, Genetics and Molecular Biology

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