227930-25-8Relevant academic research and scientific papers
Sequential radical cyclization of β-functionalized allyl bromomethyldimethylsilyl ethers. Application to the regioand stereo-specific synthesis of an isoprostanoid precursor
Belval, Florence,Fruchier, Alain,Chavis, Claude,Montera, Jean-Louis,Lucas, Marc
, p. 697 - 703 (2007/10/03)
The behaviour of allyl bromomethyldimethylsilyl ethers β-substituted by various radical trapping functions (aldehyde, nitrile or acetylenic) is studied in tandem radical cyclizations. Only homopropargylic ethers (but-3ynylic ethers) lead to the formation of cyclic compounds via a 5-exo-trig, 5-exo-dig or 5-exo-trig, 6-endo-dig mode. The influence of the TMS group located on the acetylenic moiety is shown to be determinant for the regio- and stereo-specific C5 ring closure (5-exo-clig mode).
