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Title: Catalytic asymmetric aza-Michael addition of fumaric monoacids with multifunctional thiourea/boronic acids
Authors: Michigami, Kenichi
Murakami, Hiroki
Nakamura, Takeru
Hayama, Noboru
Takemoto, Yoshiji
Author's alias: 道上, 健一
村上, 弘樹
竹本, 佳司
Issue Date: 7-Mar-2019
Publisher: Royal Society of Chemistry
Journal title: Organic and Biomolecular Chemistry
Volume: 17
Issue: 9
Start page: 2331
End page: 2335
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.
Rights: This is the accepted manuscript of the article, which has been published in final form at https://doi.org/10.1039/C9OB00045C.
The full-text file will be made open to the public on 29 January 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/242994
DOI(Published Version): 10.1039/c9ob00045c
PubMed ID: 30734817
Appears in Collections:Journal Articles

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