Enantiospecific and regioselective opening of 2-alkyl nosylaziridines by indoles mediated by boron trifluoride. Application to a practical synthesis of a GnRH …

…, RJ Alabaster, JYL Chung, B Craig, JS Edwards…

Index: Farr, Roger N.; Alabaster, Ramon J.; Chung, John Y.L.; Craig, Bridgette; Edwards, John S.; Gibson, Andrew W.; Ho, Guo-Jie; Humphrey, Guy R.; Johnson, Simon A.; Grabowski Tetrahedron Asymmetry, 2003 , vol. 14, # 22 p. 3503 - 3515

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Citation Number: 33

Abstract

An efficient, high yield process for the synthesis of a GnRH antagonist has been developed. We have demonstrated that under boron trifluoride mediation, nosyl aziridines will react with 2-arylindole derivatives to afford β-substituted tryptamines in an enantiospecific process with remarkably high regioselectivity. The scope of the reaction was explored with several 2- substituted nosyl aziridines. The key reaction was developed expressly for the GnRH ...