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KIM, Youyoung
분자활성 촉매반응 연구단
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Ring-opening functionalizations of unstrained cyclic amines enabled by difluorocarbene transfer

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Title
Ring-opening functionalizations of unstrained cyclic amines enabled by difluorocarbene transfer
Author(s)
Youyoung Kim; Joon Heo; Dongwook Kim; Sukbok Chang; Sangwon Seo
Subject
TERTIARY-AMINES, ; N-DEALKYLATION, ; ORGANIC-SYNTHESIS, ; CLEAVAGE, ; COMPLEX, ; DEMETHYLATION, ; CONVERSION, ; DIVERSITY, ; OXIDATION, ; CYANOGEN
Publication Date
2020-09-21
Journal
NATURE COMMUNICATIONS, v.11, no.1, pp.4761
Publisher
NATURE RESEARCH
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. 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.
URI
https://pr.ibs.re.kr/handle/8788114/7631
DOI
10.1038/s41467-020-18557-8
ISSN
2041-1723
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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