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Catalytic asymmetric aza-Michael addition of fumaric monoacids with multifunctional thiourea/boronic acids

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Abstract

The first chemical enantioselective synthesis of N-hydroxyaspartic acid derivatives using chiral multifunctional thiourea/boronic acid organocatalysts was developed. A series of fumaric monoacids underwent an intermolecular asymmetric aza-Michael addition of O-alkyl hydroxylamines in excellent regioselectivity. The addition of another carboxylic acid raised the enantiomeric enrichment up to 97% ee. O-Deprotection of the aza-Michael adduct provided an aspartate-derived hydroxylamine fragment applicable for KAHA (α-keto acid-hydroxylamine) ligation.

Graphical abstract: Catalytic asymmetric aza-Michael addition of fumaric monoacids with multifunctional thiourea/boronic acids

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Publication details

The article was received on 08 Jan 2019, accepted on 29 Jan 2019 and first published on 29 Jan 2019


Article type: Communication
DOI: 10.1039/C9OB00045C
Citation: Org. Biomol. Chem., 2019, Advance Article

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    Catalytic asymmetric aza-Michael addition of fumaric monoacids with multifunctional thiourea/boronic acids

    K. Michigami, H. Murakami, T. Nakamura, N. Hayama and Y. Takemoto, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00045C

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