36206-73-2Relevant academic research and scientific papers
Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles
Adamson, Nathan J.,Wilbur, Katherine C. E.,Malcolmson, Steven J.
supporting information, p. 2761 - 2764 (2018/03/06)
We report a highly enantioselective Pd-PHOX-catalyzed intermolecular hydroalkylation of acyclic 1,3-dienes. Meldrum's acid derivatives and other activated C-pronucleophiles, such as β-diketones and malononitriles, react with a variety of aryl- and alkyl-substituted dienes in ≤20 h at room temperature. The coupled products, obtained in up to 96% yield and 97.5:2.5 er, are easily transformed into useful chemical building blocks for downstream synthesis.
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
supporting information, 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.).
SYNTHESIS OF (+/-)-SENOXEPIN - THE FIRST NATURALLY OCCURING ANTI-HUECKEL OXEPIN DERIVATIVE
Cleve, A.,Bohlmann, F.
, p. 1241 - 1244 (2007/10/02)
The first total synthesis of (+/-)-senoxepin 3 is described. 3 is prepared via an intramolecular cycloaddition from a substituted decadienyne 7.The resulting hexalin 8 was converted to a lactone, which on epoxidation, NBS bromination and elimination with NaI afforded senoxepin.
