Publications by authors named "Bradley D Robertson"
Mixtures of [{PCy2(o-biphenyl)}AuCl] and AgSbF6 catalyze the tandem cycloaddition/hydroarylation of 7-aryl-1,6-enynes with electron-rich arenes to form 6,6-diarylbicyclo[3.2.0]heptanes in good yield under mild conditions.
View Article and Find Full Text PDFGold-catalyzed intermolecular anti-markovnikov hydroamination of alkylidenecyclopropanes.
Angew Chem Int Ed Engl
February 2015
The cationic gold phosphine complex [{PCy2 (o-biphenyl)}Au(NCMe)](+) SbF6 (-) (Cy=cyclohexyl) catalyzes the intermolecular, anti-Markovnikov hydroamination reaction of monosubstituted and cis- and trans-disubstituted alkylidenecyclopropanes (ACPs) with imidazolidin-2-ones and other nucleophiles. This reaction forms 1-cyclopropyl alkylamine derivatives in high yield and with high regio- and diastereoselectivity. NMR spectroscopic analysis of gold π-ACP complexes and control experiments point to the sp hybridization of the ACP internal alkene carbon atom as controlling the regiochemistry of the ACP hydroamination reaction.
View Article and Find Full Text PDFArticle Synopsis
- The study presents the first asymmetric total synthesis of apratoxin D, a powerful compound that inhibits human lung cancer cell growth with an IC(50) value of 2.6 nM.
- To achieve this, the researchers used asymmetric N-amino cyclic carbamate α,α-bisalkylation to effectively create the C-37 methyl group with high selectivity.
- Additionally, they implemented key asymmetric reactions, including Evans syn-aldol and Paterson anti-aldol transformations, both demonstrating excellent stereoselectivity.