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Título

Synthesis of highly functionalized enantiopure halocyclopropanes derived from carbohydrates

AutorRodríguez-Solla, Humberto; Concellón, Carmen; Amo, Vicente del; Díaz-Pardo, Ainhoa; Blanco, Elena G.; García-Granda, Santiago CSIC ORCID ; Díaz, M. Rosario CSIC; Llavona, Ricardo; Soengas, Raquel G.
Palabras claveCarbohydrates
Amides
Carbenoids
Chromium
Small ring systems
Fecha de publicación2013
EditorWiley-VCH
CitaciónEuropean Journal of Organic Chemistry (22): 4953-4961 (2013)
ResumenA chromium-mediated synthesis of enantiopure sugar-based halocyclopropanecarboxamides is reported. This reaction can be stereospecifically carried out on (E)- or (Z)-¿,ß-unsaturated amides and takes place with the formation of a new C-Hal stereogenic center, which is generated with total stereoselectivity. Synthetic applications of the obtained halocyclopropanecarboxamides are also reported. The structure of the halocyclopropanes and derivatives were established by X-ray analysis. A mechanism to explain these transformations is proposed. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
URIhttp://hdl.handle.net/10261/112933
DOI10.1002/ejoc.201300322
Identificadoresdoi: 10.1002/ejoc.201300322
issn: 1434-193X
e-issn: 1099-0690
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