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Synlett 2010(8): 1170-1189  
DOI: 10.1055/s-0029-1219780
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Thieme Chemistry Journal Awardees -Where Are They Now? Bicyclic Alkenes: From Cycloadditions to the Discovery of New Reactions

William Tam*, Neil Cockburn
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada
Fax: +1(519)7661499; e-Mail: wtam@uoguelph.ca;
Further Information

Publication History

Received 29 September 2009
Publication Date:
17 March 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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