期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 49, 页码 17791-17794出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b11865
关键词
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资金
- Japan Tobacco Inc. (JT)
- JSPS [17H05430]
- JSPS KAKENHI [17H06173]
- Asahi Glass Foundation
- Kobayashi International Scholarship Foundation
- Grants-in-Aid for Scientific Research [17H05430, 17H06173] Funding Source: KAKEN
Three-dimensional, small-ring scaffolds are very important in modern drug discovery to expand the available drug-like chemical space and to optimize drug candidates. Among them, bicyclo[1.1.1]pentane (BCP) is regarded as a high-value bioisostere for a phenyl ring or tert-butyl group; it provides an option to generate drug-like molecules with good passive permeability, high aqueous solubility, and improved metabolic stability, though the lack of methodology to functionalize BCP remains a significant challenge. Here we present an efficient method, developed with the aid of density functional theory calculations, for the synthesis of multifunctionalized BCP derivatives by means of a radical multicomponent carboamination of [1.1.1]propellane. This reaction features mild conditions, one-pot operation, and gram-scale synthetic capability, and opens up a unique and highly efficient route for the synthesis of multifunctionalized BCP derivatives, including synthetically useful 3-substituted BCP-amines.
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