760968-16-9Relevant academic research and scientific papers
Extending Pummerer reaction chemistry. Development of a strategy for the regio- and stereoselective oxidative cyclization of 3-(ω-nucleophile)- tethered indoles
Feldman, Ken S.,Vidulova, Daniela Boneva,Karatjas, Andrew G.
, p. 6429 - 6440 (2005)
The brominative cyclization of diastereomeric β-silyloxy tryptophan derivatives proceeded with divergent regiochemistry (C(2) or C(3) addition), depending on the relative stereochemistry of the silyloxy substituent. This lack of C(2) vs C(3) regiochemical predictability led to the development of a new approach, which featured Pummerer-type chemistry on an indole C(2) sulfoxide or sulfide substrate, for steering nucleophilic addition to C(3) of the indole. Extension of this transformation from carboxylate nucleophiles to carbon analogues such as allylsilane, silyl enol ether, and silyl ketene iminal bearing substrates led to the formation of spirocyclic oxindole derivatives in good yields with complete regioselectivity for C(3) cyclization and with good diastereoselectivity where relevant.
Extending pummerer reaction chemistry. Application to the oxidative cyclization of tryptophan derivatives
Feldman, Ken S.,Karatjas, Andrew G.
, p. 2849 - 2852 (2007/10/03)
(Equation Presented) The diastereoselective oxidative cyclization of a β-oxygenated tryptophan derivative is reported. This process, which utilizes a new variant of the Pummerer reaction, may have application in TMC-95A synthesis.
