1613740-64-9Relevant academic research and scientific papers
Alkylation of indoles by aziridinium ions: New rapid access to tetrahydro-β-carbolines (THBCs)
Menguy, Laurence,Lo, Cheikh,Marrot, Jér?me,Couty, Fran?ois
, p. 4512 - 4518 (2014/06/10)
The alkylation of indoles by aziridinium ions generated in situ from β-amino chlorides was explored. The outcome of this reaction strongly relied on the substitution pattern of the starting β-amino chloride and requires silver tetrafluoroborate activation to proceed in reasonable yield. Ephedrine- and pseudoephedrine-derived N-cyanomethyl-β-amino chlorides afforded the corresponding tryptamines in a regio- and stereoselective manner and subsequent silver(I)-promoted Pictet-Spengler reactions produced 4-phenyl substituted THBCs in good yields. Unexpected epimerization at C-3 was found in these reactions, producing trans-3,4-disubstituted THBCs stereoselectively.
