期刊
CHEMICAL & PHARMACEUTICAL BULLETIN
卷 65, 期 6, 页码 573-581出版社
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c17-00158
关键词
alpha-imino carboxylic acid derivative; heterogeneous oxidant; asymmetric organocatalysis; thiourea; unnatural alpha-amino acid
资金
- Japan Society for the Promotion of Science (JSPS) [JP16K18845]
- SUNBOR
- Grants-in-Aid for Scientific Research [16H02611] Funding Source: KAKEN
We describe herein a manganese(IV) oxide-mediated oxidation of N-p-methoxyphenyl (PMP)-protected glycine derivatives for the synthesis of alpha-imino carboxylic acid derivatives. Using this methodology, utilization of unstable glyoxic acid derivatives was avoided. Furthermore, using this methodology we synthesized novel alpha-imino carboxylic acid derivatives such as alpha-imino phenyl ester, perfluoroalkyl etsers, imides, and thioester. The asymmetric Mannich reaction of those novel imine derivatives with 1,3-dicarbonyl compound is also described, and the novel alpha-imino imide gave improved chemical yield and stereoselectivity compared with those obtained by the use of the conventional alpha-imino ester-type substrate.
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