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

Youyoung Kim, Joon Heo, Dongwook Kim, Sukbok Chang () and Sangwon Seo ()
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Youyoung Kim: Korea Advanced Institute of Science and Technology (KAIST)
Joon Heo: Korea Advanced Institute of Science and Technology (KAIST)
Dongwook Kim: Korea Advanced Institute of Science and Technology (KAIST)
Sukbok Chang: Korea Advanced Institute of Science and Technology (KAIST)
Sangwon Seo: Korea Advanced Institute of Science and Technology (KAIST)

Nature Communications, 2020, vol. 11, issue 1, 1-11

Abstract: Abstract 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.

Date: 2020
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DOI: 10.1038/s41467-020-18557-8

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