The Double [3+2] Photocycloaddition Reaction, 2011
Springer Theses Series

Jason Woolford's thesis describes for the first time, a double [3+2] photocycloaddition of alkenes onto aromatic rings. Modern synthetic chemistry relies on the ability of researchers to uncover new and more efficient ways of creating highly complex structures. This work describes a novel, environmentally friendly photochemical step that converts in one pot, trivial starting materials into otherwise difficult to construct fenstrane frameworks.  The rigid cores of these frameworks have significant potential in drug design. Moreover, the novelty of this work overtakes many other methods for the creation of chiral centres. No less than seven chiral centres are created in the photochemical step together with the formation of four carbon-carbon bonds  and multifused rings. Jason's innovative work has been the subject of several publications in peer-reviewed journals.

Introduction and background.- Discovery of the double [3+2] photocycloaddition.- A brief discussion on fenestranes.- Investigation of the double [3+2] photocycloaddition reaction for the synthesis of fenestranes.- Attempted synthesis of a “criss-cross” double [3+2] photocycloadduct.- Attempts toward the synthesis of alternative structures via the double[3+2] photocycloaddition.- Conclusion.- Experimental.- References.- Appendix I.

Jason Woolford's thesis describes for the first time, a double [3+2] photocycloaddition of alkenes onto aromatic rings. Modern snythetic chemistry relies on the ability of researchers to uncover new and more efficient ways of creating highly complex structures. This work describes a novel, environmentally friendly photochemical step that converts in one pot, trivial starting materials into otherwise difficult to construct fenstrane frameworks.  The rigid cores of these frameworks have significant potential in drug design. Moreover, the novelty of this work overtakes many other methods for the creation of chiral centres. No less than seven chiral centres are created in the photochemical step together with the formation of four carbon-carbon bonds  and multifused rings. Jason's innovative work has been the subject of several publications in peer-reviewed journals.

Nominated by the University of Sussex for a Springer Theses Prize Synthesis of fenestrane frameworks have significant potential in drug design Outlines the possibilities for the creation of further chiral centres Includes supplementary material: sn.pub/extras