910788-16-8Relevant articles and documents
Regioselective Epoxidations by Cytochrome P450 3A4 Using a Theobromine Chemical Auxiliary to Predictably Produce N-Protected β- or γ-Amino Epoxides
Polic, Vanja,Cheong, Kin Jack,Hammerer, Fabien,Auclair, Karine
, p. 3983 - 3989 (2017/11/30)
N-Protected β- and γ-amino epoxides are useful chiral synthons. We report here that the enzyme cytochrome P450 3A4 can catalyze the formation of such compounds in a regio- and stereoselective manner, even in the presence of multiple double bonds or aromatic substituents. To this end, the theobromine chemical auxiliary is used not only to control the selectivity of the enzyme, but also as a masked amine, and to facilitate product recovery. Theobromine predictably directed epoxidation at the double bond of the fourth carbon from the theobromine group. Unlike with most catalysts, the selectivity did not depend on electronic or steric factors but rather on the position of the olefin relative to the theobromine group. (Figure presented.).
Competition between alkenes in intramolecular ketene-alkene [2 + 2] cycloaddition: What does it take to win?
Belanger, Guillaume,Levesque, Francois,Paquet, Julie,Barbe, Guillaume
, p. 291 - 296 (2007/10/03)
(Chemical Equation Presented). In the course of developing a new synthetic methodology using ketenes in sequential cycloaddition steps, we were faced with a competition problem with molecules containing a ketene tethered to more than one reacting partner.