4743-70-8Relevant academic research and scientific papers
Diastereoselective carbocyclization of 1,6-heptadienes triggered by rhodium-catalyzed activation of an olefinic C-H bond
Aissa, Christophe,Ho, Kelvin Y. T.,Tetlow, Daniel J.,Pin-No, Maria
supporting information, p. 4209 - 4212 (2014/05/06)
The use of α,ω-dienes as functionalization reagents for olefinic carbon-hydrogen bonds has been rarely studied. Reported herein is the rhodium(I)-catalyzed rearrangement of prochiral 1,6-heptadienes into [2,2,1]-cycloheptane derivatives with concomitant creation of at least three stereogenic centers and complete diastereocontrol. Deuterium-labeling studies and the isolation of a key intermediate are consistent with a group-directed C-H bond activation, followed by two consecutive migratory insertions, with only the latter step being diastereoselective. Folding alkenes: Described is the first example of a rhodium(I)-catalyzed functionalization of an olefinic C-H bond with a 1,6-heptadiene reagent. This carbocyclization is completely diastereoselective and creates at least three stereogenic centers from simple prochiral substrates. The directing group can easily be converted into other functional groups.
