Methyleneaziridines: Unusual Vehicles for Organic Synthesis

Michael Shipman

doi:10.1055/s-2006-951566

ACCOUNT

Methyleneaziridines: Unusual Vehicles for Organic Synthesis

Michael Shipman*
Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK
Fax: +44(2476)524112; e-Mail: m.shipman@warwick.ac.uk;

Abstract

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Abstract

This account describes the development of methyleneaziridines as heterocyclic building blocks for a variety of useful synthetic transformations including multicomponent reactions, cycloadditions and radical cascades.

1 Introduction

2 Preparation of Methyleneaziridines

2.1 Ring Closure to Methyleneaziridines

2.2 Functionalization of Methyleneaziridines

3 Multicomponent Reactions

3.1 Ketone-Forming MCRs

3.2 Amine- and Heterocycle-Forming MCRs

3.3 α-Amino Nitrile Forming MCRs

4 [4+3] Cycloadditions

5 Radical Rearrangements

6 Conclusions

Key words

aziridines - strained heterocycles - ring opening

Full Text

References

References and Notes

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As far as we are aware, the toxicological effects of methyleneaziridines are unknown. However, since the adverse health effects of aziridines are well established, it is prudent to exercise caution in the handling of methyleneaziridines. Avoid all skin contact and perform all manipulations in a well-vented fume cupboard with adequate personal protection measures.