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Issue 6, 2018
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Direct access to spirobiisoxazoline via the double 1,3-dipolar cycloaddition of nitrile oxide with allenoate

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Abstract

The double [3 + 2]-cycloadditions between nitrile oxides and allenoates have been achieved. In the presence of DABCO combined with Et3N, 2-substituted buta-2,3-dienoates reacted with oxime chlorides to afford spirobiisoxazolines in 55–90% yields via the double 1,3-dipolar cycloaddition. Notably, the construction of double isoxazoline moieties and two chiral centers including a spiro carbon center was achieved.

Graphical abstract: Direct access to spirobiisoxazoline via the double 1,3-dipolar cycloaddition of nitrile oxide with allenoate

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Publication details

The article was received on 08 Dec 2017, accepted on 04 Jan 2018 and first published on 04 Jan 2018


Article type: Communication
DOI: 10.1039/C7OB03040A
Citation: Org. Biomol. Chem., 2018,16, 895-898
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    Direct access to spirobiisoxazoline via the double 1,3-dipolar cycloaddition of nitrile oxide with allenoate

    X. Shang, K. Liu, Z. Zhang, X. Xu, P. Li and W. Li, Org. Biomol. Chem., 2018, 16, 895
    DOI: 10.1039/C7OB03040A

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