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Issue 35, 2017
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Synthesis of phostones via DABCO-catalyzed bromocyclization of alkenylphosphonic acid monoesters

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Abstract

The bromocyclization of 4-aryl-3-butenylphosphonic acid monoesters could proceed smoothly and rapidly in CH3CN with 1.2 equiv. of NBS in the presence of 0.02 equiv. of DABCO at room temperature, giving exclusively the six-membered ring bromophostones with high endo regioselectivity but poor diastereoselectivity. The diastereomers were separated and their relative configurations were determined based on their NMR analysis and X-ray crystallography. Furthermore, we preliminarily demonstrated that the asymmetric bromocyclization of these kinds of substrates was possible.

Graphical abstract: Synthesis of phostones via DABCO-catalyzed bromocyclization of alkenylphosphonic acid monoesters

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Publication details

The article was received on 14 Jun 2017, accepted on 17 Aug 2017 and first published on 17 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01436H
Citation: Org. Biomol. Chem., 2017,15, 7396-7403

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    Synthesis of phostones via DABCO-catalyzed bromocyclization of alkenylphosphonic acid monoesters

    H. Wang, L. Huang, X. Cao, D. Liang and A. Peng, Org. Biomol. Chem., 2017, 15, 7396
    DOI: 10.1039/C7OB01436H

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