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Issue 9, 2019
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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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Article information


Submitted
24 Jan 2019
Accepted
29 Mar 2019
First published
29 Mar 2019

Green Chem., 2019,21, 2375-2379
Article type
Paper

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, 21, 2375
DOI: 10.1039/C9GC00278B

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