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Diastereodivergent synthesis of cyclopropanes via on-water [2 + 1] annulations of diazo compounds with electron-deficient alkenes

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Abstract

A highly efficient cyclopropanation of diazo compounds and electron-deficient alkenes under metal- and catalyst-free conditions was developed. The use of water as the sole solvent dramatically increased the efficiency of the reaction. This on-water synthesis approach featured numerous advantages, including high yield, broad substrate scope and environmentally friendly conditions. Moreover, a simple substrate-engineering strategy was used in the reaction system to realise the unprecedented diastereodivergent synthesis of functionalised cyclopropane derivatives with remarkable stereoselectivities.

Graphical abstract: Diastereodivergent synthesis of cyclopropanes via on-water [2 + 1] annulations of diazo compounds with electron-deficient alkenes

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Publication details

The article was received on 24 Jan 2019, accepted on 29 Mar 2019 and first published on 29 Mar 2019


Article type: Paper
DOI: 10.1039/C9GC00278B
Citation: Green Chem., 2019, Advance Article

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    Diastereodivergent synthesis of cyclopropanes via on-water [2 + 1] annulations of diazo compounds with electron-deficient alkenes

    Q. Li, X. Zhang, K. Xie, Q. Dai, R. Zeng, Y. Liu, Z. Jia, X. Feng and J. Li, Green Chem., 2019, Advance Article , DOI: 10.1039/C9GC00278B

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