Synlett
DOI: 10.1055/s-0036-1588511
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© Georg Thieme Verlag Stuttgart · New York

Heterocycles as Moderators of Allyl Cation Cycloaddition Reactivity

Jan Hullaert, Bram Denoo, Mien Christiaens, Brenda Callebaut, Johan M. Winne*
  • Organic Synthesis Research Group, Ghent University, Krijgslaan 281 S4, 9000 Gent, Belgium   Email: johan.winne@ugent.be
Further Information

Publication History

Received: 30 May 2017

Accepted after revision: 27 June 2017

Publication Date:
27 July 2017 (eFirst)

Abstract

For the rapid elaboration of polycarbocyclic scaffolds, prevalent in many important families of terpenoid natural products, allyl cations derived from simple heterocyclic alcohols can be used as versatile reaction partners in both (4+3) and (3+2) cycloaddition pathways. Our recent progress in this area is outlined, pointing towards the untapped potential of heterocycles to act as reagents in novel or known but challenging organic transformations.

1 Heterocyclic Reagents

2 Cycloadditions and Allyl Cations

3 Furfuryl Cations in Cycloadditions

4 Heterocycle-Substituted Cations in Cycloadditions

5 Mechanistic Considerations

6 Conclusions and Outlook