128936-93-6Relevant articles and documents
Mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-quinone methide
Bishop, Lee M.,Winkler, Michael,Houk, Kendall N.,Bergman, Robert G.,Trauner, Dirk
, p. 5405 - 5408 (2008)
A study was conducted to perform mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-Quinone methide (QM). The study focused on mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-Quinone methide, as led to the formation of chromenes. Vinyl o-QM was prepared through oxidation of phenol 3, while the E configuration of the exo-alkylidene bond was established by detailed nuclear magnetic resonance (NMR) studies and X-ray crystallography. The structure of the dimer was also confirmed by X-ray crystallography. Kinetic investigation of the uncatalyzed cyclization of Vinyl o-QM and chromene revealed the sensitivity of the rate of the reaction to light, oxygen, and adventitious acid, studying the reactivity of o-QM.
Enantioselective addition of boronates to o -quinone methides catalyzed by chiral biphenols
Luan, Yi,Schaus, Scott E.
supporting information, p. 19965 - 19968 (2013/02/22)
Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the pr
