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Park, Cheol-Min
Synthetic & Medicinal Chemistry Lab
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  • Organic synthesis, medicinal chemistry, chemical biology

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alpha-Diazo oxime ethers for N-heterocycle synthesis

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Title
alpha-Diazo oxime ethers for N-heterocycle synthesis
Author
Choi, SubinHa, SujinPark, Cheol-Min
Issue Date
2017-06
Publisher
ROYAL SOC CHEMISTRY
Citation
CHEMICAL COMMUNICATIONS, v.53, no.45, pp.6054 - 6064
Abstract
This Feature Article introduces the preparation and synthetic utility of α-diazo oxime ethers. α-Oximino carbenes are useful synthons for N-heterocycles, and can be easily prepared from α-diazo oxime ethers as precursors. We begin with the preparation of α-diazo oxime ethers and their application in [3+2] cycloaddition. It turns out that the nature of metals bound to carbenes plays a crucial role in modulating the reactivity of α-oximino carbenes, in which copper carbenes smoothly react with enamines, whereas the less reactive enol ethers and nitriles require gold carbenes. In Section 3.2, a discussion on N-O and C-H bond activation is presented. Carbenes derived from diazo oxime ethers show unique reactivity towards N-O and C-H bond activation, in which the proximity of the two functionalities, carbene and oxime ether, dictates the preferred reaction pathways toward pyridines, pyrroles, and 2H-azirines. In Section 3.3, the development of tandem reactions based on α-diazo oxime ethers is discussed. The nature of carbenes in which whether free carbenes or metal complexes are involved dissects the pathway and forms different types of 2H-azirines. The 2H-azirine formation turned out to be an excellent platform for the tandem synthesis of N-heterocycles including pyrroles and pyridines. In the last section, we describe the electrophilic activation of 2H-azirines with vinyl carbenes and oximino carbenes. The resulting azirinium species undergo rapid ring expansion rearrangements to form pyridines and pyrazines.
URI
https://scholarworks.unist.ac.kr/handle/201301/21987
URL
http://pubs.rsc.org/en/Content/ArticleLanding/2017/CC/C7CC02650A#!divAbstract
DOI
10.1039/C7CC02650A
ISSN
1359-7345
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