1346158-92-6Relevant articles and documents
Redox-triggered C-c coupling of alcohols and vinyl epoxides: Diastereo- and enantioselective formation of all-carbon quaternary centers via tert -(Hydroxy)-prenylation
Feng, Jiajie,Garza, Victoria J.,Krische, Michael J.
supporting information, p. 8911 - 8914 (2014/07/08)
Iridium catalyzed primary alcohol oxidation triggers reductive C-O bond cleavage of isoprene oxide to form aldehyde-allyliridium pairs that combine to form products of tert-(hydroxy)-prenylation, a motif found in >2000 terpenoid natural products. Curtin-Hammett effects are exploited to enforce high levels of anti-diastereo- and enantioselectivity in the formation of an all-carbon quaternary center. The present redox-triggered carbonyl additions occur in the absence of stoichiometric byproducts, premetalated reagents, and discrete alcohol-to-aldehyde redox manipulations.
