Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction
A unique alkene difunctionalization reaction that allows rapid construction of molecular complexity around the biologically relevant indole framework has been developed. The reaction proceeds with up to 87% yield, 99:1 er, and >20:1 dr. Evaluation of several of the compounds revealed promising anticancer activity against MCF-7 cells.
Pathak, Tejas P.,Gligorich, Keith M.,Welm, Bryan E.,Sigman, Matthew S.
supporting information; experimental part
p. 7870 - 7871
(2010/08/05)
Advancing the mechanistic understanding of an enantioselective palladium-catalyzed alkene difunctionalization reaction
The mechanism of an enantioselective palladium-catalyzed alkene difunctionalization reaction has been investigated. Kinetic analysis provides evidence of turnover-limiting attack of a proposed quinone methide intermediate with MeOH and suggests that copper is involved in productive product formation, not just catalyst turnover. Through examination of substrate electronic effects, a Jaffe relationship was observed correlating rate to electronic perturbation at two positions of the substrate. Ligand effects were evaluated to provide evidence of rapid ligand exchange between palladium and copper as well as a correlation between ligand electronic nature and enantioselectivity.
Jensen, Katrina H.,Webb, Jonathan D.,Sigman, Matthew S.
supporting information; experimental part
p. 17471 - 17482
(2011/02/27)
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