Access to 5-bromopentanal and 6-bromohexanal derivatives via the bromination/hydrolysis of C,O-bis-zirconocenes generated from unsaturated Weinreb amides
- 7 July 2022
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 20 (29) , 5803-5811
Abstract
Access to 5-bromopentanal and 6-bromohexanal derivatives from Weinreb amides is described. The method relies on the sequential C-bromination/zircona-aminal hydrolysis of bis-C,O-zirconocenes, which are generated in situ from unsaturated Weinreb amides using Schwartz's reagent. Synthetic illustrations of such bromo-aldehydes, which can act as carbocycle and heterocycle precursors, are also presented.Keywords
Funding Information
- Université de Reims Champagne-Ardenne
- Centre National de la Recherche Scientifique
This publication has 43 references indexed in Scilit:
- A Direct Stereoselective Approach totrans-2,3-Disubstituted Piperidines: Application in the Synthesis of 2-Epi-CP-99,994 and (+)-EpilupinineOrganic Letters, 2008
- Au-Catalyzed Cyclization of Monoallylic DiolsOrganic Letters, 2008
- An expeditious stereoselective synthesis of natural (−)-Cassine via cascade HWE [3 + 2]-cycloaddition processOrganic & Biomolecular Chemistry, 2005
- Hydrogen Bonding as a Construction Element for Bidentate Donor Ligands in Homogeneous Catalysis: Regioselective Hydroformylation of Terminal AlkenesJournal of the American Chemical Society, 2003
- Design, Synthesis, and Structure−Activity Relationships of Macrocyclic Hydroxamic Acids That Inhibit Tumor Necrosis Factor α Release in Vitro and in VivoJournal of Medicinal Chemistry, 2001
- A Novel and Expeditious Reduction of Tertiary Amides to Aldehydes Using Cp2Zr(H)ClJournal of the American Chemical Society, 2000
- First example of a stable 1,1-bidentate Lewis acid based on boron and zirconium: synthesis, reactivity, X-ray analysis and NMR studiesJournal of the Chemical Society, Chemical Communications, 1994
- Stereochemistry of the reversible cyclization of .omega.-formylalkyl radicalsThe Journal of Organic Chemistry, 1992
- Selective reductions. 39. Partial reduction of carboxylic acids with thexylchloroborane-methyl sulfide. A direct and simple aldehyde synthesisThe Journal of Organic Chemistry, 1987
- Synthesis of enantiomerically pure 24-alkylsterol side chains, in both enantiomeric forms, starting from (R)-(+)-limoneneThe Journal of Organic Chemistry, 1986