Recent advances in cyclohydrocarbonylation reactions
- 1 June 2005
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 83 (6-7) , 681-692
- https://doi.org/10.1139/v05-035
Abstract
This article describes recent advances in the cyclohydrocarbonylation reactions catalyzed by transition-metal complexes and their applications in organic synthesis as a review covering the relevant literature up to the middle of 2004. The reactions are categorized into four types, i.e., intramolecular amidocarbonylation reactions, intramolecular aminocarbonylation reactions, cyclohydrocarbonylation reactions involving carbon–nucleophiles, and other cyclohydrocarbonylation reactions. Cyclohydrocarbonylation reactions provide efficient routes to various monocyclic, bicyclic, and polycyclic compounds as a one-step cascade process or a one-pot process. Reaction mechanisms for these cascade processes are discussed as needed for clarification. The heterocyclic and carbocyclic compounds, thus obtained, can be further transformed to specific targets. Examples of such applications are also discussed.Key words: catalysis, cyclohydrocarbonylation, hydroformylation, amidocarbonylation, cyclization, regioselectivity, aldehydes, regioselective, cascade, heterocycles, rhodium.Keywords
This publication has 35 references indexed in Scilit:
- Domino Reactions in Organic SynthesisChemical Reviews, 1996
- Amide-directed hydrocarbonylation of N-alkenylamides and α-alkenyllactamsJournal of Organometallic Chemistry, 1991
- New synthesis of nitrogen heterocycles through amide-directed hydrocarbonylation of alkenamides catalyzed by rhodium complexesThe Journal of Organic Chemistry, 1991
- Synthesis of α,ω-Diamino Acids via Amidocarbonylation Reaction: Novel Synthesis of Lysine, Ornithine, and Their AnalogsBulletin of the Chemical Society of Japan, 1991
- Synthesis of Proline and 2-Piperidinecarboxylic Acid via Cobalt-Catalyzed Isomerization–Carbonylation of N-Acyl Unsaturated Cyclic AminesBulletin of the Chemical Society of Japan, 1991
- New routes to nitrogen heterocycles through intramolecular amidocarbonylation of alkenamides catalyzed by rhodium complexesTetrahedron Letters, 1989
- Novel amide-directed hydrocarbonylations and double carbonylation of N-allylamidesThe Journal of Organic Chemistry, 1988
- Synthesis of N-acyl-.ALPHA.-amino acids by cobalt catalyzed amido-carbonylation.Journal of Synthetic Organic Chemistry, Japan, 1988
- Synthesis of N-acyl-α-amino esters via cobalt-catalyzed carbonylation of N-acyl-α-alkoxyaminesJournal of Molecular Catalysis, 1987
- Asymmetric hydroformylation and hydrocarboxylation of enamides. Synthesis of alanine and prolineThe Journal of Organic Chemistry, 1980