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Boron-Catalyzed α-Amination of Carboxylic Acids

Takuto Morisawa, Masaya Sawamura* and Yohei Shimizu*

*Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan, Email: sawamurasci.hokudai.ac.jp, shimizu-ysci.hokudai.ac.jp

T. Morisawa, M. Sawamura, Y. Shimizu, Org. Lett., 2019, 21, 7466-7469.

DOI: 10.1021/acs.orglett.9b02769 (free Supporting Information)



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Abstract

Catalytically generated boron enolates of carboxylic acids react with diisopropylazodicarboxylate as electrophilic aminating reagent to provide amino acid derivatives. The resulting α-aminocarboxylic acids can easily be converted to carboxylic acid derivatives. Extension to a catalytic asymmetric variant was possible by introducing a chiral ligand on the boron catalyst.

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Key Words

hydrazine derivatives


ID: J54-Y2019