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通过亚胺与 2,2-二乙氧基乙酸的脱羧偶联反应合成α-氨基缩醛。

Synthesis of α-Aminoacetals via Decarboxylative Coupling of Imine and 2,2,-Diethoxyacetic Acid.

机构信息

Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 08826, Republic of Korea.

Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea.

出版信息

J Org Chem. 2023 May 19;88(10):6532-6537. doi: 10.1021/acs.joc.2c01941. Epub 2022 Nov 6.

DOI:10.1021/acs.joc.2c01941
PMID:36336846
Abstract

Atom-economical C-C coupling between imines and a C1 source could provide α-aminoaldehyde derivatives. Nevertheless, such a coupling has rarely been achieved owing to the lack of appropriate nucleophilic C1 sources. In this study, photocatalytic synthesis of α-aminoacetals was achieved via decarboxylative coupling of imine and 2,2-diethoxyacetic acid using a nonstoichiometric amount of a radical initiator. Various functional groups were compatible, providing efficient one-step access to diversely functionalized α-aminoacetals, which provides a promising platform for further research.

摘要

通过使用非化学计量的自由基引发剂,实现了亚胺与 2,2-二乙氧基乙酸的脱羧偶联,从而通过光催化合成了α-氨基缩醛。各种官能团都具有兼容性,为各种功能化的α-氨基缩醛提供了高效的一步法合成途径,为进一步的研究提供了有前景的平台。

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