Heterocycles from cyclopropanes: applications in natural product synthesis
Top Cited Papers
- 10 July 2009
- journal article
- review article
- Published by Royal Society of Chemistry (RSC) in Chemical Society Reviews
- Vol. 38 (11), 3051-3060
- https://doi.org/10.1039/b901245c
Abstract
The construction of heterocyclic compounds from activated cyclopropane derivatives offers an alternative strategy for the preparation of molecules that may be of interest from a structural or biological standpoint. Several newly developed methods provide access to densely functionalized heterocycles in a manner that can be considered useful for both diversity- and target-oriented synthetic approaches. This tutorial review focuses on the latter, describing recent developments and applications of cyclopropane ring-expansion reactions in natural product synthesis.Keywords
This publication has 60 references indexed in Scilit:
- Scope and Mechanism for Lewis Acid-Catalyzed Cycloadditions of Aldehydes and Donor−Acceptor Cyclopropanes: Evidence for a Stereospecific Intimate Ion Pair PathwayJournal of the American Chemical Society, 2008
- Scandium triflate catalyzed cycloaddition of imines with 1,1-cyclopropanediesters: efficient and diastereoselective synthesis of multisubstituted pyrrolidinesOrganic & Biomolecular Chemistry, 2005
- Diastereoselective Synthesis of Pyrrolidines via the Yb(OTf)3 Catalyzed Three-Component Reaction of Aldehydes, Amines, and 1,1-CyclopropanediestersThe Journal of Organic Chemistry, 2005
- Highly Diastereoselective Synthesis of Tetrahydrofurans via Lewis Acid-Catalyzed Cyclopropane/Aldehyde CycloadditionsThe Journal of Organic Chemistry, 2005
- Recent advances in donor–acceptor (DA) cyclopropanesTetrahedron, 2004
- A Homo [3+2] Dipolar Cycloaddition: The Reaction of Nitrones with CyclopropanesAngewandte Chemie, 2003
- Donor−Acceptor-Substituted Cyclopropane Derivatives and Their Application in Organic SynthesisChemical Reviews, 2003
- Facile, Novel Methodology for the Synthesis of Spiro[pyrrolidin-3,3′-oxindoles]: Catalyzed Ring Expansion Reactions of Cyclopropanes by AldiminesAngewandte Chemie, 1999
- Use of cyclopropanes and their derivatives in organic synthesisChemical Reviews, 1989
- Electrophilic cyclopropanes in organic synthesisAccounts of Chemical Research, 1979