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

William Tam; Neil Cockburn

doi:10.1055/s-0029-1219780

ACCOUNT

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;

Abstract

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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

Full Text

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<A NAME="RS11609ST-93A">93a</A> Cesario C. Tardibono LP. Miller MJ. J. Org. Chem. 2009, 74: 448

<A NAME="RS11609ST-93B">93b</A> Galvani G. Calvet G. Blanchard N. Kouklovsky C. Org. Biomol. Chem. 2008, 6: 1063

<A NAME="RS11609ST-93C">93c</A> Li F. Miller M.
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<A NAME="RS11609ST-93F">93f</A> Ritter AR. Miller MJ. J. Org. Chem. 1994, 59: 4602

For selected examples of oxidative cleavage of the C=C bond of 3-aza-2-oxabicyclo[2.2.1]heptenes, see:

<A NAME="RS11609ST-94A">94a</A> Nora GP. Miller MJ. Möllmann U. Bioorg. Med. Chem. Lett. 2006, 16: 3966

<A NAME="RS11609ST-94B">94b</A> Pepper AG. Procter G. Voyle M. Chem. Commun. 2002, 1066

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<A NAME="RS11609ST-95A">95a</A> Calvet G. Blanchard N. Kouklovsky C. Org. Lett. 2007, 9: 1485

<A NAME="RS11609ST-95B">95b</A> Ellis JM. King SB. Tetrahedron Lett. 2002, 43: 5833

<A NAME="RS11609ST-96">96</A> Muxworthy JP. Wilkinson JA. Procter G. Tetrahedron Lett. 1995, 36: 7535

For palladium- and Lewis acid catalyzed ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]heptenes, see:

<A NAME="RS11609ST-97A">97a</A> Lee W. Kim K.-H. Surman MD. Miller MJ.
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<A NAME="RS11609ST-97B">97b</A> Surman MD. Mulvihill MJ. Miller MJ. Org. Lett. 2002, 4: 139

<A NAME="RS11609ST-97C">97c</A> Surman MD. Miller MJ. J. Org. Chem. 2001, 66: 2466

<A NAME="RS11609ST-97D">97d</A> Surman MD. Miller MJ. Org. Lett. 2001, 3: 519

<A NAME="RS11609ST-97E">97e</A> Mulvihill MJ. Surman MD. Miller MJ. J. Org. Chem. 1998, 63: 4874

For copper-catalyzed Grignard or organozinc nucleophilic ring-opening reactions, see:

<A NAME="RS11609ST-98A">98a</A> Pineschi M. Moro FD. Crotti P. Macchia F. Pure Appl. Chem. 2006, 78: 463

<A NAME="RS11609ST-98B">98b</A> Pineschi M. Moro FD. Crotti P. Macchia F. Org. Lett. 2005, 7: 3605

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<A NAME="RS11609ST-98D">98d</A> Surman MD. Mulvihill MJ. Miller MJ. Tetrahedron Lett. 2002, 43: 1131

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<A NAME="RS11609ST-100B">100b</A> Murakami M. Igawa H. Chem. Commun. 2002, 390

<A NAME="RS11609ST-101">101</A> Machin BP. Ballantine M. Mandel J. Blanchard N. Tam W. J. Org. Chem. 2009, 74: 7261