Synthesis of Chiral Amino Acids by Using CO2 as a C1 Source

2017 Fiscal Year Final Research Report

• Project/Area Number: 26293001
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Hokkaido University
• Principal Investigator: SATO Yoshihiro 北海道大学, 薬学研究院, 教授 (90226019)
• Research Collaborator: SAITO Nozomi ; OONISHI Yoshihiro ; MITA Tsuyoshi ; DOI Ryohei
• Project Period (FY): 2014-04-01 – 2018-03-31
• Keywords: カルボキシル化反応 / αーアミノ酸 / βーアミノ酸 / 不斉合成 / ニッケル / コバルト / 二酸化炭素 / カルボン酸

Outline of Final Research Achievements

Carbon dioxide (CO2) is attractive to synthetic organic chemists as an abundant, cheap, and non-toxic carbon source. Although CO2 is very stable chemical substances, it has mainly two reactivities; one is electrophilicity of the center carbon of CO2, and the other is that C=O double bond can be activated by transition metal complexes. With respect to the former reactivity, we developed the synthesis of chiral a-amino acids through Cu-catalyzed asymmetric addition of silyl anion to N-sulfonyl imine followed by the reaction of the resultant chiral a-silyl N-sulfoneamide with CO2 in a stereoretentive manner. With respect to the latter reactivity, we developed the synthesis of a chiral b-amino acids or b-aryloxy carboxylic acids through a combination of nickel-catalyzed carboxylation of ynamides or aryl ynol ethers and rhodium-catalyzed asymmetric hydrogenation of the resultant carboxylated product.

Free Research Field

有機合成化学