Cyclization and Cycloaddition
Reactions of Cyclopropyl Carbonyls and Imines

Filippo De Simone; Jérôme Waser

doi:10.1055/s-0029-1216998

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Synthesis 2009(20): 3353-3374
DOI: 10.1055/s-0029-1216998

REVIEW

Cyclization and Cycloaddition Reactions of Cyclopropyl Carbonyls and Imines

Filippo De Simone, Jérôme Waser*
Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland
Fax: +41(21)6939700; e-Mail: jerome.waser@epfl.ch;

Further Information

Publication History

Received 15 May 2009
Publication Date:
08 September 2009 (online)

Abstract
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Abstract

Activated cyclopropanes, such as vinyl and carbonyl cyclopropanes, are useful building blocks in organic chemistry due to their exceptional reactivity. This review focuses on the use of cyclopropyl carbonyls and imines in cyclization and cycloaddition reactions for the synthesis of cyclic compounds. Cycloisomerization and other cyclization reactions are treated first, followed by formal cycloaddition reactions and applications in total synthesis. For each class of reactions, key pioneering works are briefly presented and emphasis is then set on recent results. Indeed, the utility of activated cyclopropanes in organic synthesis has increased significantly in the last few years by combining modern catalytic methods with the well-established reactivity of these building blocks. Together with progress in the synthesis of the cyclopropanes, these new methods allowed a better control over the diastereoselectivity and enantioselectivity of the reactions as well as their use for the synthesis of complex natural products.

1 Introduction and Scope of the Review

2 Cyclization Reactions

2.1 Nucleophile Attached to the Carbonyl

2.2 Nucleophile Attached to the Cyclopropane

3 Cyclization Reactions Involving Incorporation of
Exogenous Atom(s)

4 Formal [3+2]-Cycloaddition Reactions

4.1 With Olefins

4.2 With Aldehydes and Ketones

4.3 With Imines and Nitriles

4.4 With Other Electrophiles

5 Other Cycloaddition Reactions

5.1 [3+3]-Cycloaddition Reactions

5.2 [4+3]-Cycloaddition Reactions

6 Applications in Total Synthesis

7 Conclusion

Key words

activated cyclopropanes - cyclizations - cycloadditions - isomerizations - stereoselective synthesis

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26

For a more detailed discussion of the reaction mechanism, see ref. 25b.