100208-15-9Relevant articles and documents
Visible light photocatalytic asymmetric synthesis of pyrrolo[1,2-: A] indoles via intermolecular [3+2] cycloaddition
Casado-Sánchez, Antonio,Domingo-Legarda, Pablo,Cabrera, Silvia,Alemán, José
, p. 11303 - 11306 (2019)
The intermolecular diastereoselective and enantioselective synthesis of pyrrolo[1,2-a]indoles is developed through a [3+2] cycloaddition between silyl-indole derivatives and α,β-unsaturated N-acyl oxazolidinones by merging photocatalysis and Lewis acid catalysis.
A Dipolar Cycloaddition Approach to Pyrroloindoles Using N--Substituted Indoles
Padwa, Albert,Fryxell, Glen E.,Gasdaska, John R.,Venkatramanan, M. K.,Wong, George S. K.
, p. 644 - 653 (2007/10/02)
The 1,3-dipolar cyloaddition of a number of N--substituted indoles with several dipolarophiles has been investigated.The reaction requires the use of an equivalent amount of silver fluoride and provides a direct and efficient synthesis of the pyrroloindole ring system.The structures of the cycloadducts were established by high-field NMR spectroscopy as well as by several X-ray crystal structures.The cycloaddition reactions show all the characteristics of a concerted reaction, including complete stereospecificity and regioselectivity.The results are consistent with a mechanism that involves the intermediacy of an azomethine ylide.Formation of the dipole is rationalized by assuming that silver ion behaves as a very specific Lewis acid that attacks the indole ring to give a silver bonded carbonium ion.This is followed by a rapid desilylation reaction to give the azomethine ylide.After the cycloaddition step, the resulting silver-bonded intermediate undergoes consecutive loss of silver and a hydrogen to give the observed product.Attempts to extend the cycloaddition methodology to N--substituted enamines and pyrroles are also described.
