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Issue 89, 2012
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Study on the coupling of acyclic esters with alkenes – the synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide

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Abstract

The radical cyclization between aliphatic acyclic esters and alkenes was achieved unprecedentedly in the presence of allylsamarium bromide with HMPA and H2O as additives. The cascade radical cyclization–ring-opening–anionic cyclization allowed facile and efficient access to 2-(2-hydroxyalkyl)cyclopropanols from readily available materials.

Graphical abstract: Study on the coupling of acyclic esters with alkenes – the synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide

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Supplementary files

Article information


Submitted
28 Jun 2012
Accepted
18 Sep 2012
First published
19 Sep 2012

Chem. Commun., 2012,48, 11026-11028
Article type
Communication

Study on the coupling of acyclic esters with alkenes – the synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide

Y. Tu, L. Zhou, R. Yin, X. Lv, R. A. Flowers II, K. A. Choquette, H. Liu, Q. Niu and X. Wang, Chem. Commun., 2012, 48, 11026
DOI: 10.1039/C2CC34630C

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