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Interrupted Bayer-Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate.

07:00 EST 31st January 2018 | BioPortfolio

Summary of "Interrupted Bayer-Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate."

The instability of hydroxyl peroxyesters, the elusive Criegee intermediates of the Bayer-Villiger rearrangement, can be alleviated by selective deactivation of stereoelectronic effects that promote the 1,2-alkyl shift. Stable cyclic Criegee intermediates constrained within a five-membered ring can be prepared by mild reduction of respective hydroperoxyl peroxyesters (β-hydroperoxy-β-peroxylactones) which were formed in high yields in reaction of β-ketoesters with BF3·Et2O/H2O2.

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This article was published in the following journal.

Name: Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
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