392230-13-6Relevant articles and documents
Diastereoselective synthesis of 2,3,5-trisubstituted tetrahydrofurans via cyclofunctionalization reactions. Evidence of stereoelectronic effects
Guindon,Soucy,Yoakim,Ogilvie,Plamondon
, p. 8992 - 8996 (2001)
The work described herein considers the impact of stereoelectronic effects and allylic 1,3-strain in controlling the cyclofunctionalization reaction when a hydroxyl group is at the allylic position. The stereoelectronic arguments are supported by independent iodocyclization reactions performed using two secondary alcohols. The transition-state pathways involved in these reactions are established through a comparison of relative reaction rates. A bi-directional approach is used to demonstrate the potential of the iodocyclization reaction to differentiate a terminus in molecules with a pseudo C2 axis of symmetry, showing that two-directional synthesis can be used to differentiate between alternative transition-state pathways.