1080025-47-3Relevant academic research and scientific papers
Indium-promoted acyloxyallylation reaction of azetidine-2,3-diones in aqueous media: A new route to densely functionalized 3-substituted 3-hydroxy-β-lactams
Alcaide, Benito,Almendros, Pedro,Aragoncillo, Cristina,Cabrero, Gema,Callejo, Ricardo,Ruiz, M. Pilar
experimental part, p. 4434 - 4439 (2009/05/07)
Densely functionalized 3-substituted 3-hydroxy-β-lactams have been obtained by acyloxyallylation reaction of azetidine-2,3-diones with 3-bromopropenyl acetate or benzoate in aqueous media promoted by indium under Barbier conditions. Two new stereocenters were formed; the stereochemistry at the new C-3 quaternary center was fully controlled by placing a bulky chiral substituent at C-4. However, poor diastereoselectivities were observed in the new allylic stereocenter formed (up to 58% de). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
