468721-38-2Relevant articles and documents
Synthesis of CF3-Containing Spirocyclic Indolines via a Red-Light-Mediated Trifluoromethylation/Dearomatization Cascade
Gianetti, Thomas L.,Mei, Liangyong,Moutet, Jules,Stull, Savannah M.
, p. 10640 - 10653 (2021/07/31)
A red-light-mediated nPr-DMQA+-catalyzed cascade intramolecular trifluoromethylation and dearomatization of indole derivatives with Umemoto's reagent has been developed. This protocol provides a facile and efficient approach for the construction of functionalized and potentially biologically important CF3-containing 3,3-spirocyclic indolines with moderate to high yields and excellent diastereoselectivities under mild conditions. The success of multiple gram-scale (1 and 10 g) experiments further highlights the robustness and practicality of this protocol and the merit of the employment of red light. Mechanistic studies support the formation of a crucial CF3 radical species and a dearomatized benzyl carbocation intermediate.
Radical-Mediated Dearomatization of Indoles with Sulfinate Reagents for the Synthesis of Fluorinated Spirocyclic Indolines
Ryzhakov, Dmytro,Jarret, Maxime,Guillot, Régis,Kouklovsky, Cyrille,Vincent, Guillaume
, p. 6336 - 6339 (2017/12/08)
The dearomative introduction of trifluoromethyl and 1,1-difluoroethyl radicals, generated from their corresponding sulfinate salts, into the C2 position of indole derivatives allows the diastereoselective synthesis of three-dimensional 3,3-spirocyclic indolines over C-H functionalized indoles.
Preparation of β2-homotryptophan derivatives for β-peptide synthesis
Micuch, Peter,Seebach, Dieter
, p. 1567 - 1577 (2007/10/03)
In view of the prominent role of the 1H-indol-3-yl side chain of tryptophan in peptides and proteins, it is important to have the appropriately protected homologs H-β2-HTrp-OH and H-β3-HTrp-OH (Fig.) available for incorporation in β-
