1114376-70-3Relevant academic research and scientific papers
Stereoselective nickel-catalyzed cycloisomerization of 1,6-dienes
Boeing, Christian,Hahne, Julia,Francio, Giancarlo,Leitner, Walter
, p. 1073 - 1080 (2008)
Highly stereoselective cycloisomerization of 1,6-dienes with a catalyst system based on [Ni-(allyl)(cod)][BARF] and Wilke's azaphospholene all-(R)-1 is described. Unprecedented high enantiomeric excesses of up to 91% were obtained for the formation of five-membered cyclic products from symmetrically substituted 1,6-dienes. High chemo- and regioselectivities were achieved also for unsymmetrically 1,6-dienes substituted in terminal position leading again to five-membered cyclic products in fair to very good yields. Cycloisomerization products were subjected to sequential hydroboration as well as hydrogenation of the exo-methylene functional group. Promising diastereoselectivities were achieved and these reaction sequences could be efficiently performed in a one-pot procedure.
