Inokuma Tsubasa, Jichu Takahisa, Nishida Kodai, Shigenaga Akira, Otaka Akira
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University.
Chem Pharm Bull (Tokyo). 2017;65(6):573-581. doi: 10.1248/cpb.c17-00158.
We describe herein a manganese(IV) oxide-mediated oxidation of N-p-methoxyphenyl (PMP)-protected glycine derivatives for the synthesis of α-imino carboxylic acid derivatives. Using this methodology, utilization of unstable glyoxic acid derivatives was avoided. Furthermore, using this methodology we synthesized novel α-imino carboxylic acid derivatives such as α-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 α-imino imide gave improved chemical yield and stereoselectivity compared with those obtained by the use of the conventional α-imino ester-type substrate.
我们在此描述了一种二氧化锰介导的N - 对甲氧基苯基（PMP）保护的甘氨酸衍生物的氧化反应，用于合成α-亚氨基羧酸衍生物。使用该方法，避免了不稳定的乙醛酸衍生物的使用。此外，通过该方法我们合成了新型的α-亚氨基羧酸衍生物，如α-亚氨基苯基酯、全氟烷基酯、酰亚胺和硫酯。还描述了这些新型亚胺衍生物与1,3 - 二羰基化合物的不对称曼尼希反应，并且与使用传统α-亚氨基酯型底物所获得的结果相比，新型α-亚氨基酰亚胺具有更高的化学产率和立体选择性。
