Ring-opening functionalizations of unstrained cyclic amines enabled by difluorocarbene transfer

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Chemical synthesis based on the skeletal variation has been prolifically utilized as an attractive approach for modification of molecular properties. Given the ubiquity of unstrained cyclic amines, the ability to directly alter such motifs would grant an efficient platform to access unique chemical space. Here, we report a highly efficient and practical strategy that enables the selective ring-opening functionalization of unstrained cyclic amines. The use of difluorocarbene leads to a wide variety of multifaceted acyclic architectures, which can be further diversified to a range of distinctive homologative cyclic scaffolds. The virtue of this deconstructive strategy is demonstrated by successful modification of several natural products and pharmaceutical analogues. Cyclic amines are commonly present in natural products and synthetic compounds, but methods for their skeletal diversification are limited. Here, the authors report a strategy for selective ring-opening functionalization of unstrained cyclic amines to pluripotent products that can be further diversified.
Publisher
NATURE RESEARCH
Issue Date
2020-09
Language
English
Article Type
Article
Citation

NATURE COMMUNICATIONS, v.11, no.1, pp.4761

ISSN
2041-1723
DOI
10.1038/s41467-020-18557-8
URI
http://hdl.handle.net/10203/280090
Appears in Collection
CH-Journal Papers(저널논문)
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