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Traceless Electrophilic Amination for the Synthesis of Unprotected Cyclic β-Amino Acids

Jin-Sheng Yu, Miguel Espinosa, Hidetoshi Noda*, Masakatsu Shibasaki*

*Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan, Email: hnodabikaken.or.jp, mshibasabikaken.or.jp

J.-S. Yu, M. Espinosa, H. Noda, M. Shibasaki, J. Am. Chem. Soc., 2019, 141, 10530-10537.

DOI: 10.1021/jacs.9b05476


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Abstract

A Rh-catalyzed electrophilic amination of substituted isoxazolidin-5-ones provides unprotected, cyclic β-amino acids featuring either benzo-fused or spirocyclic scaffolds. Using the cyclic hydroxylamines allows for retaining both nitrogen and oxygen functionalities in the product. The traceless, redox neutral process proceeds with very low catalyst loading.

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Key Words

tetrahydroquinolines


ID: J48-Y2019