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Three-step metal-promoted allene-based preparation of bis(heterocyclic) cyclophanes from carbonyl compounds.
J Org Chem
July 2014
Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid , 28040-Madrid, Spain.
A straightforward metal-mediated method for the synthesis of bis(dihydrofuryl) cyclophane scaffolds from carbonyl compounds has been developed. The combination of the dihydrofuran moiety with different heterocycles such as β-lactams and sugars allows high levels of skeletal diversity. The process comprises indium-promoted one-pot carbonyl bis(allenylation) and gold- or palladium-catalyzed double cyclization in the resulting bis(allenols), followed by selective ruthenium-catalyzed macrocyclization.
View Article and Find Full Text PDFIndium-promoted Barbier-type allylations in aqueous media: a convenient approach to 4-C-branched monosaccharides and (1-->4)-C-disaccharides.
Carbohydr Res
December 2004
Laboratoire de Chimie Organique Multifonctionnelle, associé au CNRS (UMR 8614), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud, Bât. 420, F-91405 Orsay, France.
Starting from methyl 6-bromo-4,6-dideoxy-alpha-D-threo-4-enopyranoside, 4-C-branched sugars have been prepared through indium-promoted Barbier-type allylation of various aldehydes in aqueous media followed by hydroboration of the resulting double bond. The intermediate unsaturated monosaccharides were shown to rearrange in acidic media to give 4-C-acetyl-5-C-alkyl pyranose compounds. From beta-1-formyl sugars the corresponding beta-(1-->4)-C-disaccharides were obtained.
View Article and Find Full Text PDFIndium-Promoted Preparation of alpha-Methylene-gamma-butyrolactams from 2-(Bromomethyl)acrylic Acid and Aldimines.
J Org Chem
April 1999
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain.
Stereoselective allylation of 4-oxoazetidine-2-carbaldehydes. Application To the stereocontrolled synthesis of fused tricyclic beta-lactams via intramolecular diels-alder reaction of 2-azetidinone-tethered trienes.
J Org Chem
June 2000
Departamento de Quimica Organica I, Facultad de Quimica, Universidad Complutense, 28040-Madrid, Spain.
Allylation reactions of racemic and optically pure 4-oxoazetidine-2-carbaldehydes were investigated both under anhydrous conditions and in aqueous media. Different Lewis acid or metal mediators showed varied diastereoselectivities on product formation during allylation reactions of the above aldehydes with allyltrimethylsilane, allyltributylstannane, or allyl bromide. Under standard reaction conditions, tin(IV) chloride-promoted addition of allyltrimethylsilane to 4-oxoazetidine-2-carbaldehydes provided the highest diastereoselectivity and the best yield.
View Article and Find Full Text PDFFactors Influencing 1,4-Asymmetric Induction during Indium-Promoted Coupling of Oxygen-Substituted Allylic Bromides to Aldehydes in Aqueous Solution.
J Org Chem
May 1997
Evans Chemical Laboratories, Columbus, Ohio 43210.
The preparation and indium-promoted aldehyde addition reactions of a series of 3-substituted 3-oxy-1-bromo-2-methylidenepropanes under aqueous conditions are described. The (tert-butyldimethylsilyl)oxy derivatives 4a-d are the most diastereoselective of this group of reagents, giving rise to levels of syn-1,4-asymmetric induction in the range of 87-99%. Interestingly, syn stereoselectivity is eroded and reactions proceed more rapidly when the steric bulk of the oxygen substituent is reduced as in the hydroxy and methoxy derivatives.
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