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

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...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-07, Vol.18 (29), p.5697-577
Main Authors: Satam, Nishikant, Nemu, Saumyadip, Gururaja, Guddeangadi N, Namboothiri, Irishi N. N
Format: Article
Language:English
Subjects:
Alkenes
Conjugates
Crystallography
Furans
Ketones
NMR
Nuclear magnetic resonance
Organic compounds
Pesticides
Selectivity
Substrates
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Summary: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. Mg-Mediated conjugate addition of bromoform to electron-deficient alkenes provides tribromomethyl, dibromomethylidene or dibromocyclopropane derivatives depending on the nature of the substrate.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00599a