Smith, Elin Hopcyn (1994) Stereoselective hex-5-enyl radical cyclisations. University of Southampton, Doctoral Thesis.
Abstract
This thesis is concerned with investigating the stereoselectivity of substituted hex-5-enyl radical cyclisations.
Tandem radical cyclisations of acyclic precursors are described in the second chapter. Radical precursor (69a) cyclises to give bicyclic product (59a) in 59% yield and monocyclic product (60a) in 15% yield. Analogues of precursor (69a) having methyl substituents in different positions on the basic hex-5-enyl backbone were synthesised and cyclised. (Fig 10327A)
We observed that disubstitution leads to enhanced 1,5-cis selectivity of the first cyclisation and, consequently, to an improved yield of bicyclic material.
Chapter 3 describes the synthesis and radical cyclisation of radical precursors (101a,b and c), (89) and (104). (Fig 10327B)
These precursors were found to cyclise in a 5-exo fashion, giving rise to products which contained sterically congested bonds, with a high degree of control over the relative stereochemistry at the stereocentres formed in the cyclisation.
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