- Free-radical functionalisation of β-amino alcohols via 1,5-hydrogen atom abstraction in 1,3-oxazolidines
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Functionalisation of ethanolamine at the carbon atom α- to nitrogen can be achieved in a diastereoselective C-4 alkylation of 1,3-oxazolidines using free-radical methodology.
- Gosain, Rajendra,Norrish, Andrew M.,Wood, Mark E.
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- N-Atom Deletion in Nitrogen Heterocycles
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Excising the nitrogen in secondary amines, and coupling the two residual fragments is a skeletal editing strategy that can be used to construct molecules with new skeletons, but which has been largely unexplored. Here we report a versatile method of N-atom excision from N-heterocycles. The process uses readily available N-heterocycles as substrates, and proceeds by N-sulfonylazidonation followed by the rearrangement of sulfamoyl azide intermediates, providing various cyclic products. Examples are provided of deletion of nitrogen from natural products, synthesis of chiral O-heterocycles from commercially available chiral β-amino alcohols, formal inert C?H functionalization through a sequence of N-directed C?H functionalization and N-atom deletion reactions in which the N-atom can serve as a traceless directing group.
- Cai, Wangshui,Guo, Ting,Li, Guigen,Lu, Hongjian,Qin, Haitao,Wang, Shuang
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supporting information
p. 20678 - 20683
(2021/08/25)
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- A concise method for the functionalisation of ethanolamine α to nitrogen using free radical methodology
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A method is described for the free radical functionalisation of ethanolamine at the carbon atom α to nitrogen. The key step of the methodology is a 1,5-hydrogen atom abstraction to produce an α-aminoalkyl radical at C-4 of a 1,3-oxazolidine.
- Gosain, Rajendra,Norrish, Andrew M.,Wood, Mark E.
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p. 1399 - 1410
(2007/10/03)
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