Study of a Radical Cyclizations Cascade Leading to Bicyclo[3.1.1]heptanes.
An efficient radical cascade involving a 5-exo-dig, a 1,6-H transfer, a 6-endo-trig, a 4-exo-dig, and a final 1,6-H transfer allows the diastereoselective construction of bicyclo[3.1.1]heptanes. The size of the R substituent at the propargylic position governs the diastereoselectivity of the 6-endo-trig step. Other parameters (acetylenic substituents, unsaturated partners,.) have been investigated, and the scope and the limitations of the cascade have been delineated.
Bogen
Stéphane
S
Laboratoire de Chimie Organique de Synthèse associé au CNRS Université Pierre et Marie Curie 4, place Jussieu-Tour 44-54, Case 229, 75252 Paris Cedex 05, France.
Fensterbank
Louis
L
Malacria
Max
M