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Synthesis 2001(16): 2500-2520
DOI: 10.1055/s-2001-18713
DOI: 10.1055/s-2001-18713
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York
Titanocene Catalysed 5-exo Cyclisations of Unsaturated Epoxides- Reagent Control in Radical Chemistry
Further Information
Received
10 August 2001
Publication Date:
05 August 2004 (online)
Publication History
Publication Date:
05 August 2004 (online)
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Abstract
A synthetic route to carbocyclic and heterocyclic [3.3.0], [4.3.0] and [5.3.0] systems containing pyrrolidine and tetrahydro-furan units and various other tetrahydrofuran derivatives is presented. The products are of relevance for natural product synthesis and for the synthesis of biologically active compounds. The titanocene catalysed reactions utilises readily available unsaturated epoxides as substrates. A model explaining the diastereoselectivity of cyclisation is presented that should allow for rational design of more selective catalysts.
Key words
titanocene catatlysis - 5-exo cyclisations - epoxides - heterocyclic systems
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