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DOI: 10.1055/s-0029-1219780
Thieme Chemistry Journal Awardees -Where Are They Now? Bicyclic Alkenes: From Cycloadditions to the Discovery of New Reactions
Publikationsverlauf
Publikationsdatum:
17. März 2010 (online)
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Abstract
Recent work on synthetic applications of bicyclic alkenes is reviewed, including synthesis of substituted bicyclic alkenes, 1,3-dipolar cycloadditions, ruthenium-catalyzed [2+2] cycloadditions, ruthenium-catalyzed cyclizations and isomerizations, rhodium-catalyzed dimerizations, ruthenium- and rhodium-catalyzed ring-opening reactions.
1 Introduction
2 Synthesis of Substituted Norbornadienes and Norbornenes
2.1 Synthesis of 2- and 2,3-Disubstituted Norbornadienes by Double Lithium-Halide Exchange
2.2 Synthesis of Norbornadiene-2,3-diynes by Palladium-Catalyzed Sonogashira Coupling Reactions
2.3 Synthesis of 2,3-Diarylnorbornadienes by Palladium-Catalyzed Suzuki Coupling Reactions
2.4 Synthesis of Substituted Bicyclic Alkenes by Iron-Catalyzed Coupling Reactions
3 1,3-Dipolar Cycloadditions of Bicyclic Alkenes
3.1 Intramolecular 1,3-Dipolar Cycloadditions of Norbornadiene-Tethered Nitrile Oxides
3.2 Intramolecular 1,3-Dipolar Cycloadditions of Norbornadiene-Tethered Nitrones
4 Ruthenium-Catalyzed [2+2] Cycloadditions of Bicyclic Alkenes
4.1 Reactivity of the Alkene and the Alkyne Components
4.2 Heteroatom-Substituted Alkynes
4.3 Regioselectivities
4.4 Asymmetric Induction Studies
5 Ruthenium- and Rhodium-Catalyzed Reactions of Heterobicyclic Alkenes
5.1 Ruthenium-Catalyzed Cyclization Reactions of Oxabenzonorbornenes with Propargylic Alcohols
5.2 Ruthenium- and Rhodium-Catalyzed Isomerizations and Dimerizations of Oxabenzonorbornenes
5.3 Ruthenium- and Rhodium-Catalyzed Ring-Opening Reactions of 3-Aza-2-oxabicyclo[2.2.1]hept-5-enes
6 Conclusions
Key words
cycloaddition - ring opening - ruthenium - rhodium - bicyclic alkenes
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