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Issue 29, 2020
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Substrate-oriented selectivity in the Mg-mediated conjugate addition of bromoform to electron-deficient alkenes

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Abstract

The Mg-mediated conjugate addition of bromoform to a variety of electron-deficient alkenes has been investigated. In the case of nitrodienes and dibenzylideneacetones, tribromomethylated products were isolated, whereas spiro-cyclopropanated products were obtained with cyclic dibenzylideneketones and 3-olefinic oxindoles. The spiro-cyclopropyl ketones derived from cyclic dibenzylideneketones were successfully transformed into fused furans via the Cloke–Wilson rearrangement.

Graphical abstract: Substrate-oriented selectivity in the Mg-mediated conjugate addition of bromoform to electron-deficient alkenes

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Supplementary files

Article information


Submitted
21 Mar 2020
Accepted
04 Jul 2020
First published
06 Jul 2020

Org. Biomol. Chem., 2020,18, 5697-5707
Article type
Paper

Substrate-oriented selectivity in the Mg-mediated conjugate addition of bromoform to electron-deficient alkenes

N. Satam, S. Nemu, G. N. Gururaja and I. N. N. Namboothiri, Org. Biomol. Chem., 2020, 18, 5697
DOI: 10.1039/D0OB00599A

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