Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate
Abstract
Cyclic enol carbonates of type 2, obtained via the indium-promoted allylation of aldehydes with 4-(bromomethyl)-1,3-dioxol-2-one, undergo Heck reaction with aryl iodides in the presence of silver trifluoroacetate, to give the corresponding arylated products. Thus, 4-(bromomethyl)-1,3-dioxol-2-one can be considered as a synthetic equivalent of 3-mylhydroxyacetone enolate.
Keywords:
Allylation / Indium / Heck reaction / Aldol reaction / Organic synthesisSource:
Tetrahedron Letters, 2013, 54, 48, 6624-6626Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Note:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3493
DOI: 10.1016/j.tetlet.2013.09.115
ISSN: 0040-4039
WoS: 000326613600054
Scopus: 2-s2.0-84886791811
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Bigović, Miljan AU - Škaro, Sanja AU - Maslak, Veselin AU - Saičić, Radomir PY - 2013 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1430 AB - Cyclic enol carbonates of type 2, obtained via the indium-promoted allylation of aldehydes with 4-(bromomethyl)-1,3-dioxol-2-one, undergo Heck reaction with aryl iodides in the presence of silver trifluoroacetate, to give the corresponding arylated products. Thus, 4-(bromomethyl)-1,3-dioxol-2-one can be considered as a synthetic equivalent of 3-mylhydroxyacetone enolate. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Tetrahedron Letters T1 - Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate VL - 54 IS - 48 SP - 6624 EP - 6626 DO - 10.1016/j.tetlet.2013.09.115 ER -
@article{ author = "Bigović, Miljan and Škaro, Sanja and Maslak, Veselin and Saičić, Radomir", year = "2013", abstract = "Cyclic enol carbonates of type 2, obtained via the indium-promoted allylation of aldehydes with 4-(bromomethyl)-1,3-dioxol-2-one, undergo Heck reaction with aryl iodides in the presence of silver trifluoroacetate, to give the corresponding arylated products. Thus, 4-(bromomethyl)-1,3-dioxol-2-one can be considered as a synthetic equivalent of 3-mylhydroxyacetone enolate.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Tetrahedron Letters", title = "Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate", volume = "54", number = "48", pages = "6624-6626", doi = "10.1016/j.tetlet.2013.09.115" }
Bigović, M., Škaro, S., Maslak, V.,& Saičić, R.. (2013). Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate. in Tetrahedron Letters Pergamon-Elsevier Science Ltd, Oxford., 54(48), 6624-6626. https://doi.org/10.1016/j.tetlet.2013.09.115
Bigović M, Škaro S, Maslak V, Saičić R. Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate. in Tetrahedron Letters. 2013;54(48):6624-6626. doi:10.1016/j.tetlet.2013.09.115 .
Bigović, Miljan, Škaro, Sanja, Maslak, Veselin, Saičić, Radomir, "Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate" in Tetrahedron Letters, 54, no. 48 (2013):6624-6626, https://doi.org/10.1016/j.tetlet.2013.09.115 . .